Lithium Hydroxide → (S)-4-[(S)-4-(3-Chloro-4-trifluoromethyl-phenyl)-3-methyl-2-oxo-piperazin-1-yl]-3-hydroxy-butyric acid

HRID 2095527Notes

Reaction equation

C[O:2][C:3](=[O:27])[CH2:4][C@H:5]([OH:26])[CH2:6][N:7]1[CH2:12][CH2:11][N:10]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[C:15]([Cl:23])[CH:14]=2)[C@@H:9]([CH3:24])[C:8]1=[O:25].[OH-].[Li+]>>[Cl:23][C:15]1[CH:14]=[C:13]([N:10]2[CH2:11][CH2:12][N:7]([CH2:6][C@@H:5]([OH:26])[CH2:4][C:3]([OH:27])=[O:2])[C:8](=[O:25])[C@@H:9]2[CH3:24])[CH:18]=[CH:17][C:16]=1[C:19]([F:20])([F:21])[F:22]

Participants

Reactant 2

HCID 3939Lithium Hydroxide

HCID 67074330(S)-4-[(S)-4-(3-Chloro-4-trifluoromethyl-phenyl)-3-methyl-2-oxo-piperazin-1-yl]-3-hydroxy-butyric acid methyl ester

Product 1

HCID 67074550(S)-4-[(S)-4-(3-Chloro-4-trifluoromethyl-phenyl)-3-methyl-2-oxo-piperazin-1-yl]-3-hydroxy-butyric acidYield 82%

Procedure

In analogy to intermediate 3B, (S)-4-[(S)-4-(3-chloro-4-trifluoromethyl-phenyl)-3-methyl-2-oxo-piperazin-1-yl]-3-hydroxy-butyric acid methyl ester was hydrolyzed with 1 M aqueous lithium hydroxide (1 h) to give after extraction (EtOAc) and precipitation (dichloromethane/n-pentane) the titled compound in 82% yield as light yellow foam. MS: 393.08 (MH+)

Workup

customto give
extractionafter extraction (EtOAc) and precipitation (dichloromethane/n-pentane) the titled compound in 82% yield as light yellow foam

Sources & evidence

ORD record: ord-3318fb69616f4967a59e4e27bf5e1863
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08445674B2

Reaction notes

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