Lithium Hydroxide → (S)-2-Benzyloxycarbonylamino-4,4,4-trifluoro-butyric acid

HRID 1970651Notes

Reaction equation

HRID 1970651 reaction equation
C[O:2][C:3](=[O:21])[C@@H:4]([NH:10][C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[CH2:5][C:6]([F:9])([F:8])[F:7].[Li+].[OH-]>C1COCC1.O>[CH2:14]([O:13][C:11]([NH:10][C@@H:4]([CH2:5][C:6]([F:7])([F:9])[F:8])[C:3]([OH:21])=[O:2])=[O:12])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 66854736(S)-2-(Benzyloxycarbonylamino)-4,4,4-trifluorobutanoic acid methyl ester

Product 1

HCID 22955426(S)-2-Benzyloxycarbonylamino-4,4,4-trifluoro-butyric acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 250 mg (S)-2-Benzyloxycarbonylamino-4,4,4-trifluoro-butyric acid methyl ester in 2 ml THF and 0.5 ml water were added 20 mg LiOH at 0° C. The reaction mixture was brought to pH 3 by using Amberlite IR-120 ion exchange resin before being filtered and concentrated to give the crude title compound. Yield: 236 mg.

Workup

  1. filtrationbefore being filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-bbcce8591e6b4db996575d1d2d253c8e
Source dataset
uspto-grants-2013_04
Patent number
US08426420B2

Reaction notes

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