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Cesium carbonate → HCID 59279885, 화합물

HRID 389192
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HRID 389192 반응식
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
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참가 물질

5

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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

생성물 1

HCID 59279885HCID 59279885, 화합물수율 52.8%

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone
용매

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온도
60 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-15213fe3c31e4a75819a6d1bfb8cd583
출처 데이터셋
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08377874B2

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