5-Hydroxytetrahydropyrimidine-2(1H)-thione → 2-Thioxohexahydropyrimidin-5-yl (2R)-2-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-phenylethanoate

HRID 1761200Notes

Reaction equation

HRID 1761200 reaction equation
[F:1][C:2]1([F:18])[CH2:6][CH2:5][C@@H:4]([C@@:7]([OH:17])([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8]([OH:10])=[O:9])[CH2:3]1.O[CH:20]1[CH2:25][NH:24][C:23](=[S:26])[NH:22][CH2:21]1>>[F:1][C:2]1([F:18])[CH2:6][CH2:5][C@@H:4]([C@@:7]([OH:17])([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:8]([O:10][CH:20]2[CH2:25][NH:24][C:23](=[S:26])[NH:22][CH2:21]2)=[O:9])[CH2:3]1

Participants

3

Reactant 2

HCID 35746395-Hydroxytetrahydropyrimidine-2(1H)-thioneHCID 10890505(2R)-2-[(1R)-3,3-difluorocyclopentyl]-2-hydroxy-2-phenylacetic acid

Product 1

HCID 865973042-Thioxohexahydropyrimidin-5-yl (2R)-2-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-phenylethanoate

Procedure

Using (2R)-2-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-phenylacetic acid and 5-hydroxytetrahydropyrimidine-2(1H)-thion (cf. JP-Hei01 (1989)-128970A), the title compound was prepared by a method similar to Step 2 of Referential Example 12.

Sources & evidence

ORD record
ord-1736b7addf024f9f86c98498bbc64b2e
Source dataset
uspto-grants-2005_01
Patent number
US06846835B2

Reaction notes

Loading…