Lithium Hydroxide → (2S)-2-{[(Benzyloxy)carbonyl]amino}-4,4-difluorobutanoic acid

HRID 1185534Notes

Reaction equation

HRID 1185534 reaction equation
C[O:2][C:3](=[O:20])[C@@H:4]([NH:9][C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])[CH2:5][CH:6]([F:8])[F:7].[Li+].[OH-]>C1COCC1.O>[CH2:13]([O:12][C:10]([NH:9][C@@H:4]([CH2:5][CH:6]([F:7])[F:8])[C:3]([OH:20])=[O:2])=[O:11])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 57349058HCID 57349058, compound

Product 1

HCID 58715226(2S)-2-{[(Benzyloxy)carbonyl]amino}-4,4-difluorobutanoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 250 mg (S)-2-Benzyloxycarbonylamino-4,4-difluoro-butyric acid methyl ester in 2 ml THF was added a solution of 21 mg LiOH in 0.5 ml water at 0° C. After 2 h the mixture was brought to pH 4 by using Amberlite IR-120 ion exchange resin. The reaction mixture was filtered and concentrated and the crude product obtained used in the next step without further purification. Yield: 229 mg

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-47b2fe4282fc4ab1a11d4bf5e6cf8a6c
Source dataset
uspto-grants-2014_03
Patent number
US08669266B2

Reaction notes

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