3,3,3-Trifluoro-2-hydroxypropanoic acid → N-[3-((S)-2-Amino-1,4,5,5-tetramethyl-6-oxo-1,4,5,6-tetrahydro-pyrimidin-4-yl)-4-fluoro-phenyl]-3,3,3-trifluoro-2-hydroxy-propionamide

HRID 2409134Notes

Reaction equation

HRID 2409134 reaction equation
C(OC(=O)[NH:7][C:8]1[N:9]([CH3:26])[C:10](=[O:25])[C:11]([CH3:24])([CH3:23])[C@:12]([C:15]2[CH:20]=[C:19]([NH2:21])[CH:18]=[CH:17][C:16]=2[F:22])([CH3:14])[N:13]=1)(C)(C)C.[F:28][C:29]([F:36])([F:35])[CH:30]([OH:34])[C:31](O)=[O:32]>>[NH2:7][C:8]1[N:9]([CH3:26])[C:10](=[O:25])[C:11]([CH3:24])([CH3:23])[C@:12]([C:15]2[CH:20]=[C:19]([NH:21][C:31](=[O:32])[CH:30]([OH:34])[C:29]([F:36])([F:35])[F:28])[CH:18]=[CH:17][C:16]=2[F:22])([CH3:14])[N:13]=1

Participants

3

Reactant 2

HCID 2448963,3,3-Trifluoro-2-hydroxypropanoic acidHCID 57496584[(S)-4-(5-amino-2-fluoro-phenyl)-1,4,5,5-tetramethyl-6-oxo-1,4,5,6-tetrahydro-pyrimidin-2-yl]-carbamic acid tert-butyl ester2×

Product 1

HCID 56649994N-[3-((S)-2-Amino-1,4,5,5-tetramethyl-6-oxo-1,4,5,6-tetrahydro-pyrimidin-4-yl)-4-fluoro-phenyl]-3,3,3-trifluoro-2-hydroxy-propionamide

Procedure

The coupling of [(S)-4-(5-amino-2-fluoro-phenyl)-1,4,5,5-tetramethyl-6-oxo-1,4,5,6-tetrahydro-pyrimidin-2-yl]-carbamic acid tert-butyl ester (intermediate F2) and rac-3,3,3-trifluoro-2-hydroxy-propionic acid followed by deprotection of the intermediate yielded the title compound as a white solid. MS (ESI): m/z=405.4 [M+H]+.

Sources & evidence

ORD record
ord-cf9c28fedd9a443d8f12fc79c3ba0d3c
Source dataset
uspto-grants-2014_08
Patent number
US08815881B2

Reaction notes

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