# US 5,705,660 A · Method for the synthesis of .alpha.-oxiranyl amino acids

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- Number: US 5,705,660 A
- Document ID: US5705660A
- Status: Granted
- Kind: A
- Application number: 08/295,350
- Filed: 1994-08-22
- Granted: 1998-01-06
- Earliest claimed: 1994-08-22
- Assignees: Board of Regents, University of Nebraska-Lincoln
- Inventors: David B. Berkowitz; Michelle L. Pedersen
- Web page: https://patentgrep.com/patent/US5705660A

## CPC

- C07D 303/38: with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D 303/40: by ester radicals
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

The present invention is related to a novel class of decarboxylase enzyme inhibitors consisting of .alpha.-oxiranyl amino acids and derivatives thereof and a method of synthesizing such compounds.

## Claims

### Claim 1

A method of synthesizing .alpha.-oxiranyl amino acids, comprising:
(a) adding protective groups to the amino and carboxyl groups and to any hydroxyl and amino groups on side chains of an .alpha.-vinyl amino acid by heating said .alpha.-vinyl amino acids with benzyl chloroformate in dimethylsulfoxide in the presence of triethylamine and catalytic 4-dimethylaminopyridine;
(b) extracting and purifying the protected .alpha.-vinyl amino acid;
(c) converting the .alpha.-vinyl group of the protected .alpha.-vinyl amino acid obtained in step (b) to an .alpha.-oxiranyl group by epoxidation: and
(d) removing the protecting groups.

### Claim 2 (depends on 1)

The method of claim 1 wherein said .alpha.-vinyl amino acid is heated to approximately 50.degree. C. with benzyl chloroformate in dimethylsulfoxide in the presence of triethylamine and catalytic 4-dimethylaminopyridine.

### Claim 3 (depends on 2)

The method of claim 2 wherein said mixture is heated for approximately 1.5 hours.

### Claim 4 (depends on 1)

The method of claim 1 wherein said epoxidation is a direct epoxidation.

### Claim 5 (depends on 4)

The method of claim 4 wherein said direct epoxidation comprises mixing said protected amino acid with meta-chloroperoxybenzoic acid.

### Claim 6 (depends on 1)

The method of claim 1 wherein said epoxidation is an indirect epoxidation.

### Claim 7 (depends on 6)

The method of claim 6 wherein said indirect epoxidation comprises the steps of first converting the vinyl group to the diastereomeric erythro and threo vicinal diols through the agency of osmium tetroxide, and then separating the erythro and threo diastereomers by silica gel chromatography and then transforming these diastereomers individually to the respective epoxide by regiospecific mesylation of the less hindered primary hydroxyl group using methanesulfonyl chloride in pyridine-dichloromethane followed by treatment with lithium diisopropylamide in tetrahydrofuran to give the diastereomerically homogenous epoxide.

### Claim 8 (depends on 1)

The method of claim 1 wherein said protected groups are removed by hydrogenation in the presence of a palladium catalyst.