Methanol → tert-butyl (2S)-2-amino-3-(4-fluorophenyl)propanoate hydrochloride

HRID 751670Notes

Reaction equation

HRID 751670 reaction equation
CO.C([Cl:6])(=O)C.[C:7]([O:11][C:12](=[O:30])[C@@H:13]([NH:22]C(OC(C)(C)C)=O)[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1)([CH3:10])([CH3:9])[CH3:8]>C(OCC)(=O)C>[ClH:6].[C:7]([O:11][C:12](=[O:30])[C@@H:13]([NH2:22])[CH2:14][C:15]1[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=1)([CH3:10])([CH3:8])[CH3:9]

Participants

5

Reactant 3

HCID 887MethanolHCID 6367Acetyl chlorideHCID 59753641HCID 59753641, compound

Product 1

HCID 67278629tert-butyl (2S)-2-amino-3-(4-fluorophenyl)propanoate hydrochloride

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A stirred solution of ethyl acetate (10 mL) and methanol (0.60 mL, 14.7 mmol) was cooled to 0° C. under an argon atmosphere. Acetyl chloride (1.05 mL, 14.7 mmol) was added dropwise, and the solution warmed to rt and stirred for 30 min. 2-(S)-tert-butoxycarbonylamino-3-(4-fluorophenyl)propionic acid tert-butyl ester (Preparation 113, 1 g, 2.95 mmol) was added, and the reaction mixture stirred at rt for 4 h. The reaction mixture was filtered, washed several times with diethyl ether and dried under vacuum to give the title compound. δH (DMSO): 1.30 (9H, s), 3.01 (1H, dd), 3.20 (1H, dd), 4.08 (1H, m), 7.15 (2H, m), 7.32 (2H, m), 8.64 (3H, br s).

Workup

  1. stirringthe reaction mixture stirred at rt for 4 h
  2. filtrationThe reaction mixture was filtered
  3. washwashed several times with diethyl ether
  4. customdried under vacuum

Sources & evidence

ORD record
ord-517c3309d8c94e48ab9c197694417b00
Source dataset
uspto-grants-2008_07
Patent number
US07405210B2

Reaction notes

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