Production of mixed acid anhydride and amide compound
AssigneeSumitomo Chemical Company, Limited
InventorsTakashi Miki, Hideki Ushio, Isao Kurimoto
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Abstract
There is disclosed an advantageous mixed acid anhydride production method of formula (1): R1C(O)OY(O)n(R2)p (1) wherein R1, R2 and Y denote the same as defined below, n and p denote an integer of 1 or 2, which is characterized by adding a carboxylic acid of formula (2); R1COOH (2) wherein R1 denotes a hydrogen atom, an optionally substituted alkyl group or the like, an organic base to a solution of a carboxylic acid activating agent of formula (3); (R2)pY(O)nX (3) wherein R2 denotes an optionally substituted aliphatic hydrocarbyl group or the like, Y denotes a carbon atom, a phosphorus atom, or a sulfur atom, and X denotes a chlorine atom or the like.
Claims11
A method for producing an amide compound of formula (4);
- wherein R1 denotes
- a hydrogen atom,
- an optionally substituted saturated or unsaturated hydrocarbyl group, or
- an optionally substituted hetero ring,
- R3 and R4 independently denote
- a hydrogen atom,
- an optionally substituted saturated or unsaturated hydrocarbyl group,
- an optionally substituted hetero ring,
- a protective group for an amino group, or
- R3 represents a group of formula:
- —OR30, or —NR30R31, wherein R30 represents an optionally substituted alkyl group, or an optionally substituted aryl group and R31 represents a hydrogen atom or an optionally substituted aryl group, and
- R3 and R4 may be bonded to form a ring, which comprises reacting the mixed acid anhydride of formula (1)
- R1C(O)OY(O)n(R2)p (1)
- wherein R1 is the same as defined above, and R2, Y, n and p are the same as defined below, with an amine of formula (5);
- NHR3R4 (5)
- wherein R3 and R4 independently denote the same as described above, and wherein the mixed acid anhydride of formula (1) is prepared by adding a carboxylic acid of formula (2);
- R1COOH (2)
- wherein R1 is the same as defined above;
- and
- N-methylmorpholine to a solution of a carboxylic acid activating agent of formula (3);
- (R2)pY(O)nX (3)
- wherein R2 denotes
- an optionally substituted alkyl group,
- an optionally substituted aryl group,
- an optionally substituted chain or cyclic alkoxy group, or
- an optionally substituted aryloxy group,
- Y denotes
- a carbon atom, a phosphorus atom, or a sulfur atom,
- X denotes
- a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a cyano group or a group of formula:
- (R2)pY(O)nO—,
- wherein R2 is the same as defined above,
- n and p are an integer of 1 or 2;
- and
- when Y is a carbon atom, n=1 and p=1,
- when Y is a phosphorous atom, n=1 and p=2, and
- when Y is sulfur atom, n=2 and p=1 and R2 denotes an optionally substituted alkyl or aryl group.
A method for producing an amide compound of formula (4);
- wherein R1 denotes the same group as described below,
- R3 and R4 independently denote:
- a hydrogen atom,
- an optionally substituted saturated or unsaturated hydrocarbyl group,
- an optionally substituted hetero ring,
- a protective group for an amino group, or
- R3 represents a group of formula:
- —OR30, or —NR30R31, wherein R30 represents an optionally substituted alkyl group, or an optionally substituted aryl group and R31 represents a hydrogen atom or an optionally substituted aryl group, and R3 and R4 may be bonded to form a ring,
- which comprises reacting a mixed anyhydride with an amine of formula (5):
- NHR3R4 (5)
- wherein R3 and R4 independently denote the same as described above, optionally in the presence of a base;
- and wherein the mixed anhydride is obtained by adding a carboxylic acid of formula (2);
- R1COOH (2)
- wherein R1 denotes:
- a hydrogen atom,
- an optionally substituted saturated or unsaturated hydrocarbyl group, or an optionally substituted hetero ring
- and N-methylmorpholine to a solution of a carboxylic acid activating agent.
A method according to claim 3, wherein R1 represents a group of formula (6):
- R11R12N—A— (6)
- wherein R11 and R12 are the same as defined in claim 5, and “A” represents an alkylene group, an alkenylene group, an alkynylene group, an arylene group, an aralkylene group, arylalkenylene group, arylalkynylene group, an oxazole ring, a thiazole ring, or an imidazole ring.
Dependencies are inferred from the claim text.