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

HRID 1620897Notes

Reaction equation

HRID 1620897 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-35d9e67a15f548ca8e8cd1f3322379d3
Source dataset
uspto-grants-2014_07
Patent number
US08772336B2

Reaction notes

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