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Cesium carbonate → HCID 59279885、化合物

HRID 1875376
ノート
印刷プレビュー

反応式

HRID 1875376 の反応式
C([O-])([O-])=O.[Cs+].[Cs+].BrC1C=CC(S([O:17][C@@H:18]2[CH2:22][N:21]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C@H:20]([C:30]([O:32][CH3:33])=[O:31])[CH2:19]2)(=O)=O)=CC=1.[Br:34][C:35]1[CH:36]=[C:37]2[C:42](=[CH:43][C:44]=1[O:45][CH3:46])[NH:41][C:40](=[O:47])[CH:39]=[C:38]2O>CN1C(=O)CCC1>[Br:34][C:35]1[CH:36]=[C:37]2[C:42](=[CH:43][C:44]=1[O:45][CH3:46])[NH:41][C:40](=[O:47])[CH:39]=[C:38]2[O:17][C@H:18]1[CH2:22][N:21]([C:23]([O:25][C:26]([CH3:27])([CH3:28])[CH3:29])=[O:24])[C@H:20]([C:30]([O:32][CH3:33])=[O:31])[CH2:19]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

Cs2CO3 (8.42 g, 25.8 mmol) was added 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. The mixture was then heated to 60° C. for 6.5 hours, cooled to RT and partitioned between water and EtOAc. The organic layer was washed with water and brine, dried over MgSO4, and the solvent removed in vacuo. The crude product (6.5 g) was purified on silica (gradient elution, 0-100% EtOAc/hexane, then 0-5% MeOH/DCM) to yield the title compound (2.26 g). LRMS ESI+ ((M-Boc)+H)+ 397.3/399.3.

後処理

  1. temperaturecooled 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 removed in vacuo
  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-bf12f175b23c460a9adab67dab8ef5f6
出典データセット
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08309540B2

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