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Cesium carbonate → 1-acetoxyethyl 4-((2R,3S,4R,5S)-3-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-fluorophenyl)-4-cyano-5-neopentylpyrrolidine-2-carboxamido)-3-methoxybenzoate

HRID 882354
ノート
印刷プレビュー

反応式

HRID 882354 の反応式
[C:1]([O:4][CH:5](I)[CH3:6])(=[O:3])[CH3:2].[Cl:8][C:9]1[C:10]([F:49])=[C:11]([C@@H:15]2[C@:19]([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=3[F:29])([C:20]#[N:21])[C@H:18]([CH2:30][C:31]([CH3:34])([CH3:33])[CH3:32])[NH:17][C@H:16]2[C:35]([NH:37][C:38]2[CH:46]=[CH:45][C:41]([C:42]([OH:44])=[O:43])=[CH:40][C:39]=2[O:47][CH3:48])=[O:36])[CH:12]=[CH:13][CH:14]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.C(OCC)(=O)C>[Cl:8][C:9]1[C:10]([F:49])=[C:11]([C@@H:15]2[C@:19]([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=3[F:29])([C:20]#[N:21])[C@H:18]([CH2:30][C:31]([CH3:33])([CH3:34])[CH3:32])[NH:17][C@H:16]2[C:35]([NH:37][C:38]2[CH:46]=[CH:45][C:41]([C:42]([O:44][CH:5]([O:4][C:1](=[O:3])[CH3:2])[CH3:6])=[O:43])=[CH:40][C:39]=2[O:47][CH3:48])=[O:36])[CH:12]=[CH:13][CH:14]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 150238621-Iodoethyl acetateHCID 53358942Idasanutlin

生成物 1

HCID 717388081-acetoxyethyl 4-((2R,3S,4R,5S)-3-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-fluorophenyl)-4-cyano-5-neopentylpyrrolidine-2-carboxamido)-3-methoxybenzoate収率 65%

試薬・触媒・溶媒 2

HCID 6228
Dimethylformamide
溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

To a mixture of the above 1-iodoethyl acetate (311 mg, 1.457 mmol) and chiral 4-((2R,3S,4R,5S)-3-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-fluorophenyl)-4-cyano-5-neopentylpyrrolidine-2-carboxamido)-3-methoxybenzoic acid (US20100152190A1, 201.7 mg, 0.327 mmol) in dimethylformamide (6 mL) was added cesium carbonate (659 mg, 2.00 mmol) and the mixture was stirred at room temperature for 16 h. The reaction mixture was taken up in ethyl acetate, washed with water and then brine. The organic layer was dried over sodium sulfate and concentrated to dryness. The crude material was purified by flash chromatography (hexane/ethyl acetate, 80/20 to 20/80) to give 1-acetoxyethyl 4-((2R,3S,4R,5S)-3-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-fluorophenyl)-4-cyano-5-neopentylpyrrolidine-2-carboxamido)-3-methoxybenzoate (149.4 mg, 65% yield). MS (ES+) m/z calcd. for C35H36Cl2F2N3O6: [(M+H)+]: 702.19, found: 702.4

後処理

  1. washwashed with water
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated to dryness
  4. customThe crude material was purified by flash chromatography (hexane/ethyl acetate, 80/20 to 20/80)

出典と根拠

ORDレコード
ord-dee51e3c7f724ad2aaeea4412fc68526
出典データセット
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08993614B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート