Back to results
US 2026/0176238 A1Published application
Method for producing alkylsilyloxy-substituted benzylamine compound
AssigneeSekisui Medical Co., Ltd.
InventorShou ISHIKAWA
Life of this patent
Estimating the term…
Abstract
A method for producing a ketimine compound of formula (3) in which one to five of R1b to R5b each represent hydroxyalkyloxy having 1-16 carbon atoms, the remaining groups each represent hydrogen or halogen, for example, and RB represents hydrogen, hydroxy, or alkoxy having 1-6 carbon atoms, for example), wherein a silazane compound is subjected to a reaction with a benzoyl compound of formula (2) in which R1b to R5b and RB are as described above)), and then the resulting product is subjected to a reaction with an acid or a base.
Claims7
1:
- A method for producing a ketimine compound of general formula (3):
- in which one to five of R1b to R5b each represent a hydroxyalkyloxy group having 1-16 carbon atoms, the remaining groups each represent a hydrogen atom, a halogen atom, an alkyl group having 1-4 carbon atoms, or an alkoxy group having 1-4 carbon atoms, and
- RB represents a hydrogen atom, a hydroxyl group, an alkoxy group having 1-6 carbon atoms, or a group of the following formula:
- one to five of R1b to R5b each represent a hydroxyalkyloxy group having 1-16 carbon atoms, and the remaining groups each represent a hydrogen atom, a halogen atom, an alkyl group having 1-4 carbon atoms, or an alkoxy group having 1-4 carbon atoms, or when RB represents a structure of this formula, R5b may form an ether bond (—O—) together with R5b in formula (3). *. represents a bonding site to RB.)),
- wherein a silazane compound is subjected to a reaction with a benzoyl compound of general formula (2):
- in which one to five of R1b to R5b each represent a hydroxyalkyloxy group having 1-16 carbon atoms, the remaining groups each represent a hydrogen atom, a halogen atom, an alkyl group having 1-4 carbon atoms, or an alkoxy group having 1-4 carbon atoms, and
- RB represents a hydrogen atom, a hydroxy group, an alkoxy group having 1-6 carbon atoms, or a group of
- one to five of R1b to R5b each represent a hydroxyalkyloxy group having 1-16 carbon atoms, and the remaining groups each represent a hydrogen atom, a halogen atom, an alkyl group having 1-4 carbon atoms, or an alkoxy group having 1-4 carbon atoms, or when RB represents a structure of this formula, R5b may form an ether bond (—O—) together with R5b in formula (2) * represents a bonding site to RB.,
- and then the resulting product is subjected to a reaction with an acid or a base.
6 more elements
2:
- A method for producing a benzylamine compound of general formula (4):
- in which one to five of R1b to R5b each represent a hydroxyalkyloxy group having 1-16 carbon atoms, the remaining groups each represent a hydrogen atom, a halogen atom, an alkyl group having 1-4 carbon atoms, or an alkoxy group having 1-4 carbon atoms, and
- RB represents a hydrogen atom, a hydroxy group, an alkoxy group having 1-6 carbon atoms, or a group of the following formula:
- one to five of R1b to R5b each represent a hydroxyalkyloxy group having 1-16 carbon atoms, and the remaining groups each represent a hydrogen atom, a halogen atom, an alkyl group having 1-4 carbon atoms, or an alkoxy group having 1-4 carbon atoms, or when RB represents a structure of this formula, R5b may form an ether bond (—O—) together with R5b in formula (4). * . represents a bonding site to RB.,
- wherein a silazane compound is subjected to a reaction with a benzoyl compound of general formula (2):
- in which one to five of R1b to R5b each represent a hydroxyalkyloxy group having 1-16 carbon atoms, the remaining groups each represent a hydrogen atom, a halogen atom, an alkyl group having 1-4 carbon atoms, or an alkoxy group having 1-4 carbon atoms, and
- RB represents a hydrogen atom, a hydroxy group, an alkoxy group having 1-6 carbon atoms, or a group of
- one to five of R1b to R5b each represent a hydroxyalkyloxy group having 1-16 carbon atoms, and the remaining groups each represent a hydrogen atom, a halogen atom, an alkyl group having 1-4 carbon atoms, or an alkoxy group having 1-4 carbon atoms, or when RB represents a structure of this formula, R5b may form an ether bond (—O—) together with R5b in formula (2). * represents a bonding site to RB.,
- then causing the resulting product to react with an acid or a base to obtain a ketimine compound of general formula (3):
- in which one to five of R1b to R5b each represent a hydroxyalkyloxy group having 1-16 carbon atoms, the remaining groups each represent a hydrogen atom, a halogen atom, an alkyl group having 1-4 carbon atoms, or an alkoxy group having 1-4 carbon atoms, and
- RB represents a hydrogen atom, a hydroxy group, an alkoxy group having 1-6 carbon atoms, or a group of the following formula:
- one to five of R1b to R5b each represent a hydroxyalkyloxy group having 1-16 carbon atoms, and the remaining groups each represent a hydrogen atom, a halogen atom, an alkyl group having 1-4 carbon atoms, or an alkoxy group having 1-4 carbon atoms, or when RB represents a structure of this formula, R5b may form an ether bond (—O—) together with R5b in formula (3). *. represents a bonding site to RB., and
- causing the obtained ketimine compound to react with a reducing agent and an Fmoc-forming agent.
10 more elements
3:
- A method for producing an alkylsilyloxy-substituted benzylamine compound of general formula (5):
- in which one to five of R1c to R5c each represent an alkyloxy group having 1-29 carbon atoms and having 1-3 alkylsilyloxy groups as substituents, the remaining groups each represent a hydrogen atom, a halogen atom, an alkyloxy group having 1-4 carbon atoms, or an alkoxy group having 1-4 carbon atoms, and
- RC represents a hydrogen atom, a hydroxy group, an alkoxy group having 1-6 carbon atoms, or a group of the following formula:
- one to five of R1c to R5c each represent an alkyloxy group having 1-29 carbon atoms and having 1-3 alkylsilyloxy groups as substituents, and the remaining groups each represent a hydrogen atom, a halogen atom, an alkyl group having 1-4 carbon atoms, or an alkoxy group having 1-4 carbon atoms, or when RC represents a structure of this formula, R5c may form an ether bond (—O—) together with R5c in formula (5). * represents a bonding site to RC.)),
- wherein a silazane compound is subjected to a reaction with a benzoyl compound of general formula (2):
- in which one to five of R1b to R5b each represent a hydroxyalkyloxy group having 1-16 carbon atoms, the remaining groups each represent a hydrogen atom, a halogen atom, an alkyl group having 1-4 carbon atoms, or an alkoxy group having 1-4 carbon atoms, and
- RB represents a hydrogen atom, a hydroxy group, an alkoxy group having 1-6 carbon atoms, or a group of
- one to five of R1b to R5b each represent a hydroxyalkyloxy group having 1-16 carbon atoms, and the remaining groups each represent a hydrogen atom, a halogen atom, an alkyl group having 1-4 carbon atoms, or an alkoxy group having 1-4 carbon atoms, or when RB represents a structure of this formula, R5b may form an ether bond (—O—) together with R5b in formula (2). *. represents a bonding site to RB.,
- then causing the resulting product to react with an acid or a base to obtain a ketimine compound of general formula (3):
- in which one to five of R1b to R5b each represent a hydroxyalkyloxy group having 1-16 carbon atoms, the remaining groups each represent a hydrogen atom, a halogen atom, an alkyl group having 1-4 carbon atoms, or an alkoxy group having 1-4 carbon atoms, and
- RB represents a hydrogen atom, a hydroxy group, an alkoxy group having 1-6 carbon atoms, or a group of the following formula:
- one to five of R1b to R5b each represent a hydroxyalkyloxy group having 1-16 carbon atoms, and the remaining groups each represent a hydrogen atom, a halogen atom, an alkyl group having 1-4 carbon atoms, or an alkoxy group having 1-4 carbon atoms, or when RB represents a structure of this formula, R5b may form an ether bond (—O—) together with R5b in formula (3). * . represents a bonding site to RB.,
- causing the obtained ketimine compound to react with a reducing agent and an Fmoc-forming agent to obtain a benzylamine compound of general formula (4):
- in which one to five of R1b to R5b each represent a hydroxyalkyloxy group having 1-16 carbon atoms, the remaining groups each represent a hydrogen atom, a halogen atom, an alkyl group having 1-4 carbon atoms, or an alkoxy group having 1-4 carbon atoms, and
- RB represents a hydrogen atom, a hydroxy group, an alkoxy group having 1-6 carbon atoms, or a group of the following formula:
- one to five of R1b to R5b each represent a hydroxyalkyloxy group having 1-16 carbon atoms, and the remaining groups each represent a hydrogen atom, a halogen atom, an alkyl group having 1-4 carbon atoms, or an alkoxy group having 1-4 carbon atoms, or when RB represents a structure of this formula, R5b may form an ether bond (—O—) together with R5b in formula (4). * . represents a bonding site to RB.)),
- and then causing the benzylamine compound to react with an alkylsilylating agent.
14 more elements
4:
- The production method according to claim 1, wherein the benzoyl compound of general formula (2) is obtained by causing a halogenated alcohol to react with a compound of general formula (1):
- in which one to five of R1a to R5a each represent a hydroxy group, the remaining groups each represent a hydrogen atom, a halogen atom, an alkyl group having 1-4 carbon atoms, or an alkoxy group having 1-4 carbon atoms, and
- RA represents a hydrogen atom, a hydroxy group, an alkoxy group having 1-6 carbon atoms, or a group of the following formula:
- (one to five of R1a to R5a each represent a hydroxy group, and the remaining groups each represent a hydrogen atom, a halogen atom, an alkyl group having 1-4 carbon atoms, or an alkoxy group having 1-4 carbon atoms, or when RA represents a structure of this formula, R5a may form an ether bond (—O—) together with R5a in formula (1). * represents a bonding site to RA.
1 more element
5:
- A compound of general formula (6):
- in which one to five of R1b to R5b each represent a hydroxyalkyloxy group having 1-16 carbon atoms, the remaining groups each represent a hydrogen atom, a halogen atom, an alkyl group having 1-4 carbon atoms, or an alkoxy group having 1-4 carbon atoms, and
- RB represents a hydrogen atom, a hydroxy group, an alkoxy group having 1-6 carbon atoms, or a group of the following formula:
- one to five of R1b to R5b each represent a hydroxyalkyloxy group having 1-16 carbon atoms, and the remaining groups each represent a hydrogen atom, a halogen atom, an alkyl group having 1-4 carbon atoms, or an alkoxy group having 1-4 carbon atoms, or when RB represents a structure of this formula, R5b may form an ether bond (—O—) together with R5b in formula (6). *. represents a bonding site to RB.), and
- NY represents an imino group (═NH) or NHFmoc.
2 more elements
6:
- A method for producing an alkylsilyloxy-substituted benzylamine compound of general formula (5):
- in which one to five of R1c to R5c each represent an alkyloxy group having 1-29 carbon atoms and having 1-3 alkylsilyloxy groups as substituents, the remaining groups each represent a hydrogen atom, a halogen atom, an alkyloxy group having 1-4 carbon atoms, or an alkoxy group having 1-4 carbon atoms, and
- RC represents a hydrogen atom, a hydroxy group, an alkoxy group having 1-6 carbon atoms, or a group of the following formula:
- one to five of R1c to R5c each represent an alkyloxy group having 1-29 carbon atoms and having 1-3 alkylsilyloxy groups as substituents, and the remaining groups each represent a hydrogen atom, a halogen atom, an alkyl group having 1-4 carbon atoms, or an alkoxy group having 1-4 carbon atoms, or when Rc represents a structure of this formula, R5c may form an ether bond (—O—) together with R5c in formula (5). * represents a bonding site to RC.,
- wherein an alkylsilylating agent is subjected to a reaction with a benzylamine compound of general formula (4):
- in which one to five of R1b to R5b each represent a hydroxyalkyloxy group having 1-16 carbon atoms, the remaining groups each represent a hydrogen atom, a halogen atom, an alkyl group having 1-4 carbon atoms, or an alkoxy group having 1-4 carbon atoms, and
- RB represents a hydrogen atom, a hydroxy group, an alkoxy group having 1-6 carbon atoms, or a group of the following formula:
- one to five of R1b to R5b each represent a hydroxyalkyloxy group having 1-16 carbon atoms, and the remaining groups each represent a hydrogen atom, a halogen atom, an alkyl group having 1-4 carbon atoms, or an alkoxy group having 1-4 carbon atoms, or when RB represents a structure of this formula, R5b may form an ether bond (—O—) together with R5b in formula (4). * . represents a bonding site to RB.
5 more elements
7:
- A method for producing an alkylsilyloxy-substituted benzylamine compound of general formula (5):
- in which one to five of R1c to R5c each represent an alkyloxy group having 1-29 carbon atoms and having 1-3 alkylsilyloxy groups as substituents, the remaining groups each represent a hydrogen atom, a halogen atom, an alkyloxy group having 1-4 carbon atoms, or an alkoxy group having 1-4 carbon atoms, and
- RC represents a hydrogen atom, a hydroxy group, an alkoxy group having 1-6 carbon atoms, or a group of the following formula:
- one to five of R1c to R5c each represent an alkyloxy group having 1-29 carbon atoms and having 1-3 alkylsilyloxy groups as substituents, and the remaining groups each represent a hydrogen atom, a halogen atom, an alkyl group having 1-4 carbon atoms, or an alkoxy group having 1-4 carbon atoms, or when Rc represents a structure of this formula, R5c may form an ether bond (—O—) together with R5c in formula (5). * represents a bonding site to RC.,
- wherein a reducing agent and an Fmoc-forming agent are subjected to a reaction with a ketimine compound of general formula (3):
- in which one to five of R1b to R5b each represent a hydroxyalkyloxy group having 1-16 carbon atoms, the remaining groups each represent a hydrogen atom, a halogen atom, an alkyl group having 1-4 carbon atoms, or an alkoxy group having 1-4 carbon atoms, and
- RB represents a hydrogen atom, a hydroxy group, an alkoxy group having 1-6 carbon atoms, or a group of the following formula:
- one to five of R1b to R5b each represent a hydroxyalkyloxy group having 1-16 carbon atoms, and the remaining groups each represent a hydrogen atom, a halogen atom, an alkyl group having 1-4 carbon atoms, or an alkoxy group having 1-4 carbon atoms, or when RB represents a structure of this formula, R5b may form an ether bond (—O—) together with R5b in formula (3). * . represents a bonding site to RB.)) to obtain a benzylamine compound of general formula (4):
- in which one to five of R1b to R5b each represent a hydroxyalkyloxy group having 1-16 carbon atoms, the remaining groups each represent a hydrogen atom, a halogen atom, an alkyl group having 1-4 carbon atoms, or an alkoxy group having 1-4 carbon atoms, and
- RB represents a hydrogen atom, a hydroxy group, an alkoxy group having 1-6 carbon atoms, or a group of the following formula:
- one to five of R1b to R5b each represent a hydroxyalkyloxy group having 1-16 carbon atoms, and the remaining groups each represent a hydrogen atom, a halogen atom, an alkyl group having 1-4 carbon atoms, or an alkoxy group having 1-4 carbon atoms, or when RB represents a structure of this formula, R5b may form an ether bond (—O—) together with R5b in formula (4). *. represents a bonding site to RB.,
- and then causing the benzylamine compound to react with an alkylsilylating agent.
9 more elements