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Cesium carbonate → HCID 59279885, compound

HRID 2045707
Notes
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Reaction equation

HRID 2045707 reaction equation
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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 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

Product 1

HCID 59279885HCID 59279885, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 13387
N-methyl-2-pyrrolidone
Solvent

Conditions

Temperature
60 °C

Procedure

Cs2CO3 (8.42 g, 25.8 mmol) was added to a solution of 1-tert-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 nitrogen. The mixture was then heated to 60° C. After 6.5 h, the reaction was extracted with water and EtOAc. The organic layer was extracted with water and brine and dried over MgSO4. The solvent was then removed in vacuo. The crude product (6.5 g) was purified on silica (gradient elution, 0-100% EtOAc/hexanes, and then 0-5% MeOH/DCM) to yield 2.26 g (53%) of the title compound. LRMS ESI+ ((M-Boc)+H)+ 397.3/399.3.

Workup

  1. extractionthe reaction was extracted with water and EtOAc
  2. extractionThe organic layer was extracted with water and brine
  3. dry with materialdried over MgSO4
  4. customThe solvent was then removed in vacuo
  5. customThe crude product (6.5 g) was purified on silica (
  6. washgradient elution, 0-100% EtOAc/hexanes

Sources & evidence

ORD record
ord-bef46001d7c84355aa519de1f1fe297d
Source dataset
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08591878B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes