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Cesium carbonate → HCID 59279885、化合物

HRID 389192
ノート
印刷プレビュー

反応式

HRID 389192 の反応式
BrC1C=CC(S([O:11][C@@H:12]2[CH2:16][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C@H:14]([C:24]([O:26][CH3:27])=[O:25])[CH2:13]2)(=O)=O)=CC=1.[Br:28][C:29]1[CH:30]=[C:31]2[C:36](=[CH:37][C:38]=1[O:39][CH3:40])[NH:35][C:34](=[O:41])[CH:33]=[C:32]2O.C([O-])([O-])=O.[Cs+].[Cs+]>CN1C(=O)CCC1>[Br:28][C:29]1[CH:30]=[C:31]2[C:36](=[CH:37][C:38]=1[O:39][CH3:40])[NH:35][C:34](=[O:41])[CH:33]=[C:32]2[O:11][C@H:12]1[CH2:16][N:15]([C:17]([O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:18])[C@H:14]([C:24]([O:26][CH3:27])=[O:25])[CH2:13]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 565904841-(tert-Butyl) 2-methyl (2S,4S)-4-(((4-bromophenyl)sulfonyl)oxy)pyrrolidine-1,2-dicarboxylateHCID 592798516-Bromo-4-hydroxy-7-methoxyquinolin-2(1H)-one

生成物 1

HCID 59279885HCID 59279885、化合物収率 52.8%

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
60 °C

実験手順

To a solution of 1-t-butyl 2-methyl (2S,4S)-4-{[(4-bromophenyl)sulfonyl]oxy}pyrrolidine-1,2-dicarboxylate (4 g, 8.61 mmol) and the product from Step 1 (3.49 g, 12.92 mmol) in NMP (86 mL) under N2 was added Cs2CO3 (8.42 g, 25.8 mmol) and the mixture heated to 60° C. After 6.5 hours, the reaction was cooled to RT and partitioned between water and EtOAc. The organic layer was washed with water and brine, dried over MgSO4 and the solvent evaporated. The crude product (6.5 g) was purified on silica (gradient elution, 0-100% EtOAc/hexane and then 0-5% MeOH/DCM) to yield 2.26 g of the title compound. LRMS ESI+ ((M-Boc)+H)+ Calcd. 397.3 Found 399.3.

後処理

  1. temperaturethe reaction was cooled to RT
  2. custompartitioned between water and EtOAc
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over MgSO4
  5. customthe solvent evaporated
  6. customThe crude product (6.5 g) was purified on silica (
  7. washgradient elution, 0-100% EtOAc/hexane

出典と根拠

ORDレコード
ord-15213fe3c31e4a75819a6d1bfb8cd583
出典データセット
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08377874B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート