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

HRID 23932ノート

反応式

HRID 23932 の反応式
[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]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 6367Acetyl chlorideHCID 7047003ethyl (3S)-3-amino-3-(3-fluorophenyl)propanoate

生成物 1

HCID 59985529Ethyl (3S)-3-(acetamido)-3-(3-fluorophenyl)propanoate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-4a28208ee50140249aa1c10954802943
出典データセット
uspto-grants-2005_02
特許番号
US06855724B2

反応ノート

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