Hydrochloric Acid → Ethyl (3S)-3-(acetamido)-3-(3-fluorophenyl)propanoate

HRID 23932Notes

Reaction equation

[C:1](Cl)(=[O:3])[CH3:2].[NH2:5][C@H:6]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=1)[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9].O.Cl>ClCCl>[C:1]([NH:5][C@H:6]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=1)[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

Acetyl chloride (7.9 ml, 111 mmol) in dichloromethane (50 ml) was added dropwise to a cold (0° C.) solution of ethyl (3S)-3-amino-3-(3-fluorophenyl)propanoate (WO99/31099, Scheme 3 page 97) (25.2 g, 102 mmol) in dichloromethane (200 ml). The reaction was stirred for 2 hours at 0° C., then water (100 ml) was added. The reaction mixture was adjusted to pH 1 with 2 N hydrochloric acid and the organic layer separated. The dichloromethane layer was washed with saturated sodium hydrogencarbonate solution (50 ml), water (50 ml) and then dried (MgSO4). Solvent was evaporated under reduced pressure to afford a thick oil which was purified by column chromatography (silica gel, eluting with diethyl ether) to give the title compound as a clear, colourless oil, 25.1 g.

Workup

customthe organic layer separated
washThe dichloromethane layer was washed with saturated sodium hydrogencarbonate solution (50 ml), water (50 ml)
dry with materialdried (MgSO4)
customSolvent was evaporated under reduced pressure
customto afford a thick oil which
customwas purified by column chromatography (silica gel, eluting with diethyl ether)

Sources & evidence

ORD record: ord-4a28208ee50140249aa1c10954802943
Source dataset: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06855724B2

Reaction notes

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