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Cesium carbonate → HCID 59279885, compound

HRID 389192
Notes
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Reaction equation

HRID 389192 reaction equation
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
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 52.8%

Reagents, catalysts & solvents 1

HCID 13387
N-methyl-2-pyrrolidone
Solvent

Conditions

Temperature
60 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-15213fe3c31e4a75819a6d1bfb8cd583
Source dataset
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08377874B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes