Lithium Hydroxide → N-(tert-Butoxycarbonyl)-3-[6-(trifluoromethyl)pyridin-3-yl]-L-alanine

HRID 2075395Notes

Reaction equation

HRID 2075395 reaction equation
[Li+].[OH-].[C:3]([O:7][C:8]([NH:10][C@@H:11]([CH2:16][C:17]1[CH:18]=[N:19][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:21][CH:22]=1)[C:12]([O:14]C)=[O:13])=[O:9])([CH3:6])([CH3:5])[CH3:4]>>[C:3]([O:7][C:8]([NH:10][C@@H:11]([CH2:16][C:17]1[CH:18]=[N:19][C:20]([C:23]([F:26])([F:24])[F:25])=[CH:21][CH:22]=1)[C:12]([OH:14])=[O:13])=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

3

Reactant 2

HCID 3939Lithium HydroxideHCID 57634158Methyl N-(tert-butoxycarbonyl)-3-[6-(trifluoromethyl)pyridin-3-yl]-L-alaninate

Product 1

HCID 57950747N-(tert-Butoxycarbonyl)-3-[6-(trifluoromethyl)pyridin-3-yl]-L-alanineYield 66%

Procedure

To a LiOH solution (1.0 M in 1:1:1 water:MeOH:THF, 75 mL) was added (S)-methyl 2-(tert-butoxycarbonylamino)-3-(6-(trifluoromethyl)pyridin-3-yl)propanoate (3.8 g, 10.9 mmol). The reaction was stirred at room temperature for 30 minutes. The organic solvent in the reaction mixture was evaporated. The residue was diluted with EtOAc, washed with saturated ammonium chloride (2×100 mL), and dried over sodium sulfate. The solvent was removed to provide the product as a white solid (2.4 g, 66%). LCMS (API-ES) m/z (%): 335.0 (100%, M+H+).

Workup

  1. customThe organic solvent in the reaction mixture was evaporated
  2. additionThe residue was diluted with EtOAc
  3. washwashed with saturated ammonium chloride (2×100 mL)
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was removed

Sources & evidence

ORD record
ord-ecdb278de2ce47d2af3d08b205dce22a
Source dataset
uspto-grants-2011_04
Patent number
US07919504B2

Reaction notes

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