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

HRID 1351229Notes

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 pH1 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-b83548592815492c9c5724449e4295dc
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07217721B2

Reaction notes

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