Triethylamine → HCID 58641354、化合物

HRID 1394950ノート

反応式

HRID 1394950 の反応式
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1)=[O:3].[CH:14]1([C@H:17]([NH2:39])[C:18]([N:20]2[CH2:24][C:23]([C:25]3[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:26]=3[F:32])=[CH:22][C@H:21]2[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[O:19])[CH2:16][CH2:15]1.C(N(CC)CC)C>ClCCl>[CH:14]1([C@H:17]([NH:39][C:2](=[O:3])[O:4][C:5]2[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=2)[C:18]([N:20]2[CH2:24][C:23]([C:25]3[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:26]=3[F:32])=[CH:22][C@H:21]2[C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)=[O:19])[CH2:16][CH2:15]1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 821294-Nitrophenyl chloroformateHCID 6102824HCID 6102824、化合物

生成物 1

HCID 58641354HCID 58641354、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
23 °C

実験手順

A solution of 4-nitrophenyl chloroformate (188 mg, 0.931 mmol, 1.10 equiv) in dichloromethane (5 mL) was added dropewise to a solution of (1S)-1-cyclopropyl-2-[(2S)-4-(2,5-difluorophenyl)-2-phenyl-2,5-dihydro-1H-pyrrol-1-yl]-2-oxoethanamine (16-7, 300 mg, 0.847 mmol, 1 equiv) and triethylamine (0.354 mL, 2.54 mmol, 3.00 equiv) in dichloromethane (10 mL) at 0° C. The reaction mixture was warmed to 23° C. and stirred for 20 hours. The reaction mixture was then partitioned between saturated aqueous sodium bicarbonate solution (50 mL) and ethyl acetate (75 mL). The organic layer was washed with brine, then dried over magnesium sulfate and concentrated to provide 4-nitrophenyl(1S)-1-cyclopropyl-2-[(2S)-4-(2,5-difluorophenyl)-2-phenyl-2,5-dihydro-1H-pyrrol-1-yl]-2-oxoethylcarbamate (31-1) as a pale yellow solid. LRMS m/z (M+H) 520.5 found, 520.2 required.

後処理

  1. customThe reaction mixture was then partitioned between saturated aqueous sodium bicarbonate solution (50 mL) and ethyl acetate (75 mL)
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-56d87ddb267442b8bd403e8c631b8ec6
出典データセット
uspto-grants-2008_03
特許番号
US07348440B2

反応ノート

読み込み中…