Dimethyl Sulfoxide → HCID 59985490、化合物

HRID 23934ノート

反応式

HRID 23934 の反応式
[F:1][C:2]1[CH:3]=[C:4]([C@@H:8]([NH:12][C:13](=[O:15])[CH3:14])[CH2:9][CH2:10][OH:11])[CH:5]=[CH:6][CH:7]=1.CS(C)=O.C(N(CC)CC)C>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([C@@H:8]([NH:12][C:13](=[O:15])[CH3:14])[CH2:9][CH:10]=[O:11])[CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 59985487N-[(1S)-1-(3-Fluorophenyl)-3-hydroxypropyl]acetamide

生成物 1

HCID 59985490HCID 59985490、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Pyridine sulfur trioxide complex (37.7 g, 237 mmol) was added portionwise over 20 minutes to a stirred cold (0° C.) solution of N-[(1S)-1-(3-fluorophenyl)-3-hydroxypropyl]acetamide (25 g, 118 mmol), DMSO (16.5 ml, 233 mmol) and triethylamine (33 ml, 237 mmol) in dichloromethane (240 ml). After two hours stirring at room temperature, solvent was evaporated under reduced pressure and the residue applied directly to a silica gel column. Eluting with a gradient system starting with ethyl acetate:dichloromethane (50:50 by volume) then ethyl acetate:dichloromethane (80:20 by volume) and finally ethyl acetate gave the title compound as a colourless oil which solidified on standing (13.9 g).

後処理

  1. customsolvent was evaporated under reduced pressure
  2. washEluting with a gradient system

出典と根拠

ORDレコード
ord-2632265afe964a43bf960e376dbd2309
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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