Lithium Hydroxide → N-(2,2,2-Trifluoro-1-phenylethyl)-L-leucine

HRID 1880488Notes

Reaction equation

HRID 1880488 reaction equation
[F:1][C:2]([F:21])([F:20])[CH:3]([NH:10][C@H:11]([C:16]([O:18]C)=[O:17])[CH2:12][CH:13]([CH3:15])[CH3:14])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Li+].[OH-]>C1COCC1.CO>[F:1][C:2]([F:20])([F:21])[CH:3]([NH:10][C@H:11]([C:16]([OH:18])=[O:17])[CH2:12][CH:13]([CH3:15])[CH3:14])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 67298723HCID 67298723, compound

Product 1

HCID 57446944N-(2,2,2-Trifluoro-1-phenylethyl)-L-leucine

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a room temperature solution of methyl N-(2,2,2-trifluoro-1-phenylethyl)-L-leucinate (150 mg, 0.50 mmol) in 2:1 THF/MeOH was added 1M LiOH. The mixture was stirred overnight and concentrated. The residue was partitioned between ethyl acetate and pH 3.5 phosphate buffer. The organic phase was washed with brine, dried over MgSO4 and concentrated to give N-(2,2,2-trifluoro-1-phenylethyl)-L-leucine.

Workup

  1. concentrationconcentrated
  2. customThe residue was partitioned between ethyl acetate and pH 3.5 phosphate buffer
  3. washThe organic phase was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-20218c8b50a140288540b9659be316ba
Source dataset
uspto-grants-2012_11
Patent number
US08318748B2

Reaction notes

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