23138-53-6 → rac-4-{[(2S,3S,4S)-2,3-bis-(4-chloro-2-fluoro-phenyl)-3-cyano-4-(2,2-dimethyl-propyl)-pyrrolidine-1-carbonyl]-amino}-benzoic acid methyl ester

HRID 909040ノート

反応式

HRID 909040 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:12]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=3[F:22])([C:13]#[N:14])[CH:11]([CH2:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:10][NH:9]2)=[C:4]([F:28])[CH:3]=1.[CH3:29][O:30][C:31](=[O:41])[C:32]1[CH:37]=[CH:36][C:35]([N:38]=[C:39]=[O:40])=[CH:34][CH:33]=1>C(Cl)Cl>[CH3:29][O:30][C:31](=[O:41])[C:32]1[CH:33]=[CH:34][C:35]([NH:38][C:39]([N:9]2[CH2:10][C@@H:11]([CH2:23][C:24]([CH3:25])([CH3:27])[CH3:26])[C@@:12]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=3[F:22])([C:13]#[N:14])[C@H:8]2[C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=2[F:28])=[O:40])=[CH:36][CH:37]=1

参加物

4

反応物 2

HCID 28045423138-53-6HCID 67095473rac-(2S,3S,4S)-2,3-bis(4-chloro-2-fluoro-phenyl)-4-(2,2-dimethyl-propyl)-pyrrolidine-3-carbonitrile

生成物 1

HCID 67095319rac-4-{[(2S,3S,4S)-2,3-bis-(4-chloro-2-fluoro-phenyl)-3-cyano-4-(2,2-dimethyl-propyl)-pyrrolidine-1-carbonyl]-amino}-benzoic acid methyl ester収率 67.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A mixture of rac-(2S,3S,4S)-2,3-bis(4-chloro-2-fluoro-phenyl)-4-(2,2-dimethyl-propyl)-pyrrolidine-3-carbonitrile (150.0 mg, 0.35 mmol) and 4-isocyanato-benzoic acid methyl ester (Aldrich, 86.0 mg, 0.53 mmol) in CH2Cl2 (5 mL) was stirred at rt for 3 h. The reaction mixture was then concentrated and purified by flash column to give rac-4-{[(2S,3S,4S)-2,3-bis-(4-chloro-2-fluoro-phenyl)-3-cyano-4-(2,2-dimethyl-propyl)-pyrrolidine-1-carbonyl]amino}-benzoic acid methyl ester (141.6 mg, 66.6%) which was used in the next step without further purification.

後処理

  1. concentrationThe reaction mixture was then concentrated
  2. custompurified by flash column

出典と根拠

ORDレコード
ord-12f0ecde0ee747528f841824988e131f
出典データセット
uspto-grants-2011_09
特許番号
US08017607B2

反応ノート

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