# US 10,308,612 B2 · Method for producing 1-(acyloxy)alkyl carbamate derivative

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- Number: US 10,308,612 B2
- Document ID: US10308612B2
- Status: Granted
- Kind: B2
- Application number: 15/739,361
- Filed: 2016-06-24
- Published: 2018-06-21
- Granted: 2019-06-04
- Earliest claimed: 2015-06-26
- Assignees: Daiichi Sankyo Company, Limited
- Applicants: Daiichi Sankyo Company, Limited
- Inventors: Tsuyoshi Ueda; Yuzo Abe
- Web page: https://patentgrep.com/patent/US10308612B2

## CPC

- C07D 233/64: with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
- C07B 43/06: of amide groups
- C07C 68/06: from organic carbonates
- C07C 69/96: Esters of carbonic or haloformic acids
- C12P 17/14: Nitrogen or oxygen as hetero atom and at least one other diverse hetero ring atom in the same ring
- C12P 41/00: Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
- C07B 61/00: Other general methods
- C07B 2200/13: Crystalline forms, e.g. polymorphs
- C12Y 301/01003: Triacylglycerol lipase (3.1.1.3)
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C07B: GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR (preparation of carboxylic acid esters by telomerisation C07C67/47; telomerisation C08F)
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C12P: FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE {(brewing of beer C12C; producing vinegar C12J; producing specific peptides or proteins C07K; producing enzymes C12N9/00; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification C12N15/00; measuring or testing processes involving enzymes or microorganisms C12Q; measuring or testing processes involving nucleic acid amplification reactions C12Q1/6844; fermentation processes to form a food composition, A21 or A23; compounds in general, see the relevant compound class, e.g. C01, C07)}
- C12Y: ENZYMES

## Abstract

A method for producing a 1-(acyloxy)alkyl carbamate derivative (III), using a fluorous alkyl carbonate derivative (I), and a fluorous alkyl carbonate derivative (I) and a method for producing the same. In the formula, R1 represents C1-C4 alkyl group or a C3-C6 cycloalkyl group, R2 represents a C1-C4 alkyl group or a hydrogen atom, and A represents a fluorous alkyl group (wherein the fluorous alkyl group represents a C2-C11 alkyl group in which 40% or more of the hydrogen atoms are replaced by fluorine atoms).

## Claims

### Claim 1

A compound of formula (I):
wherein R1 is a C1-C4 alkyl group or a C3-C6 cycloalkyl group,
R2 is a C1-C4 alkyl group or a hydrogen atom,
A is a fluorous alkyl group, and
the fluorous alkyl group is a C2-C11 alkyl group in which 40% or more of the hydrogen atoms are replaced by fluorine atoms.

### Claim 2 (depends on 1)

The compound of claim 1, wherein the fluorous alkyl group is a 1,1,1,3,3,3-hexafluoro-2-propyl group.

### Claim 3 (depends on 1)

The compound of claim 1, wherein R1 is an isopropyl group and R2 is a methyl group.

### Claim 4 (depends on 1)

The compound of claim 1, wherein the compound is a compound of formula (VI):

### Claim 5 (depends on 1)

The compound of claim 1, wherein the compound is a compound of formula (VIII):

### Claim 6

A method of producing a compound of formula (I):
comprising allowing a compound of formula (IV):
to come into contact with a compound of formula (V):
wherein R1 is a C1-C4 alkyl group or a C3-C6 cycloalkyl group,
R2 is a C1-C4 alkyl group or a hydrogen atom,
A is a fluorous alkyl group, and
the fluorous alkyl group is a C2-C11 alkyl group in which 40% or more of the hydrogen atoms are replaced by fluorine atoms.

### Claim 7 (depends on 6)

The method of claim 6, wherein the fluorous alkyl group is a 1,1,1,3,3,3-hexafluoro-2-propyl group.

### Claim 8 (depends on 6)

The method of claim 6, wherein R1 is an isopropyl group and R2 is a methyl group.

### Claim 9

A method of producing a compound of formula (VI):
comprising allowing a compound of formula (XI):
to react with an enzyme in an inert solvent to hydrolyze a compound of formula (VIII):
and then removing a product obtained by the hydrolysis,
wherein the enzyme is configured to selectively hydrolyze the compound of formula (VIII).

### Claim 10 (depends on 9)

The method of claim 9, wherein the enzyme is lipase derived from Candida antarctica, lipase derived from Candida rugosa, or lipase derived from Themomyces lanuginosus.

### Claim 11 (depends on 10)

The method of claim 10, wherein the enzyme is lipase derived from Candida antarctica.

### Claim 12 (depends on 11)

The method of claim 11, wherein the enzyme is CHIRAZYME L-2,C4.

### Claim 13 (depends on 9)

The method of claim 9, wherein the inert solvent is a solvent comprising a buffer.

### Claim 14 (depends on 9)

The method of claim 9, wherein the inert solvent is a solvent comprising a phosphate buffer.