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

HRID 1351229ノート

反応式

HRID 1351229 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 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.

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-b83548592815492c9c5724449e4295dc
出典データセット
uspto-grants-2007_05
特許番号
US07217721B2

反応ノート

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