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

HRID 598904Notes

Reaction equation

HRID 598904 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-8c6368d6b2644c4e95a6e7a772723a8b
Source dataset
uspto-grants-2011_03
Patent number
US07897619B2

Reaction notes

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