(2R)-2-[(1R)-3,3-difluorocyclopentyl]-2-hydroxy-2-phenylacetic acid → ((4S)-2-thioxohexahydropyrimidin-4-yl)methyl(2R)-2-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-phenylethanoate

HRID 1761199Notes

Reaction equation

HRID 1761199 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[CH2:20][C@@H:21]1[CH2:26][CH2:25][NH:24][C:23](=[S:27])[NH:22]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][CH2:20][C@@H:21]2[CH2:26][CH2:25][NH:24][C:23](=[S:27])[NH:22]2)=[O:9])[CH2:3]1

Participants

3

Reactant 2

HCID 10890505(2R)-2-[(1R)-3,3-difluorocyclopentyl]-2-hydroxy-2-phenylacetic acidHCID 55299570(4S)-4-(hydroxymethyl)tetrahydropyrimidine-2(1H)-thione

Product 1

HCID 86597303((4S)-2-thioxohexahydropyrimidin-4-yl)methyl(2R)-2-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-phenylethanoate

Procedure

Using (2R)-2-((1R)-3,3-difluorocyclopentyl)-2-hydroxy-2-phenylacetic acid and (4S)-4-(hydroxymethyl)tetrahydropyrimidine-2(1H)-thione, the title compound was prepared by a method similar to Step 2 of Referential Example 12.

Sources & evidence

ORD record
ord-e47a249d252648b18c4b7273b96edc64
Source dataset
uspto-grants-2005_01
Patent number
US06846835B2

Reaction notes

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