# US 8,785,690 B2 · Thioamide compound, method for producing thioamide compound, method for producing [(4R,6R)-6-aminoethyl-1,3-dioxan-4-yl]acetate derivative, and method for producing atorvastatin

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- Number: US 8,785,690 B2
- Document ID: US8785690B2
- Status: Granted
- Kind: B2
- Application number: 13/971,186
- Filed: 2013-08-20
- Published: 2013-12-19
- Granted: 2014-07-22
- Earliest claimed: 2011-02-21
- Assignees: Microbial Chemistry Research Foundation
- Applicants: Microbial Chemistry Research Foundation
- Inventors: Masakatsu Shibasaki; Naoya Kumagai
- Web page: https://patentgrep.com/patent/US8785690B2

## CPC

- C07C 327/42: to hydrogen atoms or to carbon atoms of a saturated carbon skeleton
- A61P 3/06: Antihyperlipidemics
- A61P 13/08: of the prostate
- A61P 19/10: for osteoporosis
- A61P 25/28: for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- C07B 53/00: Asymmetric syntheses
- C07D 207/337: 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 207/34: with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07F 7/1804: {Compounds having Si-O-C linkages (Si-O-acyl linkages C07F7/1896)}
- Y02P 20/55: Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07B: GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR (preparation of carboxylic acid esters by telomerisation C07C67/47; telomerisation C08F)
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## Abstract

A thioamide compound represented by the following general formula (1): wherein, in the general formula (1), R1 represents one of —OR11 and —NR12R13; R2 and R3 each independently represent one of a protecting group of an amide group and a hydrogen atom; the R11 represents one of a protecting group of a hydroxyl group and a hydrogen atom; and the R12 and R13 each independently represent one of a protecting group of an amino group and a hydrogen atom, where the R12 and R13 may together form a protecting group having a cyclic structure.

## Claims

### Claim 1

A thioamide compound represented by the following general formula (1):
wherein, in the general formula (1), R1 represents one of —OR11 and —NR12R13; R2 and R3 each independently represent one of a protecting group of an amide group and a hydrogen atom; the R11 represents one of a protecting group of a hydroxyl group and a hydrogen atom; and the R12 and R13 each independently represent one of a protecting group of an amino group and a hydrogen atom, where the R12 and R13 may together form a protecting group having a cyclic structure.

### Claim 2

A method for producing a thioamide compound represented by the following general formula (1), the method comprising:
reacting a compound represented by the following general formula (2) with a compound represented by the following general formula (3) to obtain the thioamide compound represented by the following general formula (1):
wherein, in the general formula (1), R1 represents one of —OR11 and —NR12R13; R2 and R3 each independently represent one of a protecting group of an amide group and a hydrogen atom; the R11 represents one of a protecting group of a hydroxyl group and a hydrogen atom; and the R12 and R13 each independently represent one of a protecting group of an amino group and a hydrogen atom, where the R12 and R13 may together form a protecting group having a cyclic structure,
wherein, in the general formula (2), R1 represents one of —OR11 and —NR12R13; the R11 represents one of a protecting group of a hydroxyl group and a hydrogen atom; the R12 and R13 each independently represent one of a hydrogen atom and a protecting group of an amino group, where the R12 and R13 may together form a protecting group having a cyclic structure; and in the general formula (3), R2 and R3 each independently represent one of a protecting group of an amide group and a hydrogen atom.

### Claim 3 (depends on 2)

The method for producing the thioamide compound according to claim 2, wherein the reacting is carried out with a copper complex.

### Claim 4 (depends on 3)

The method for producing the thioamide compound according to claim 3, wherein the copper complex is a copper-optically active phosphine complex.

### Claim 5

A method for producing atorvastatin, comprising:
converting a thioamide compound represented by the following general formula (1) into an acetate derivative represented by the following general formula (4) and converting the acetate derivative represented by the following general formula (4) into atorvastatin:
wherein, in the general formula (1), R1 represents one of —OR11 and —NR12R13; R2 and R3 each independently represent one of a protecting group of an amide group and a hydrogen atom; the R11 represents one of a protecting group of a hydroxyl group and a hydrogen atom; and the R12 and R13 each independently represent one of a protecting group of an amino group and a hydrogen atom, where the R12 and R13 may together form a protecting group having a cyclic structure, and
wherein, in the general formula (4), R4 represents one of a protecting group of a carboxyl group and a hydrogen atom; and R5 and R6 each independently represent one of a hydrocarbon group having 1 to 6 carbon atoms and a hydrogen atom, where the R5 and R6 may together form a cyclic structure.