Ammonium Hydroxide → Phenylalanine amide

HRID 2067335Notes

Reaction equation

HRID 2067335 reaction equation
Cl.C[O:3][C:4](=O)[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[NH2:6].[OH-].[NH4+:16]>O>[NH2:6][C@@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:4]([NH2:16])=[O:3]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 75736Methyl L-phenylalaninate hydrochloride

Product 1

HCID 445694Phenylalanine amideYield 59%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of L-phenylalanine methyl ester hydrochloride (6.50 g, 30.1 mmol) and ammonium hydroxide solution (28% in water, 15 mL) in water (60 mL) was stirred at ambient temperature for 64 h. The aqueous layer was extracted with dichloromethane (6×100 mL), and the combined organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to afford (S)-2-amino-3-phenylpropanamide as a colorless solid in 59% yield (2.92 g): 1H NMR (300 MHz, DMSO-d6) δ 7.38-7.21 (m, 5H), 7.12 (br s, 1H), 5.44 (br s, 1H), 3.63 (dd, J=9.5, 3.9 Hz, 1H), 3.28 (dd, J=13.7, 3.9 Hz, 1H), 2.72 (dd, J=13.7, 9.5 Hz, 1H), 1.41 (br s, 2H).

Workup

  1. extractionThe aqueous layer was extracted with dichloromethane (6×100 mL)
  2. dry with materialthe combined organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f09dec965e0a4616aac7ad9b115ed35a
Source dataset
uspto-grants-2012_10
Patent number
US08293768B2

Reaction notes

Loading…