2-(1-Ethoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-4-(4-nitro-benzoyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester → 4-Nitro-benzoic acid 5-(1-ethoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-pyrrolidin-3-yl ester

HRID 407591Notes

Reaction equation

HRID 407591 reaction equation
C(OC([N:8]1[CH2:12][CH:11]([O:13][C:14](=[O:24])[C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)[CH2:10][CH:9]1[C:25](=[O:37])[NH:26][C:27]1([C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH2:29][CH:28]1[CH:30]=[CH2:31])=O)(C)(C)C>FC(F)(F)S(O)(=O)=O.ClCCl>[CH2:35]([O:34][C:32]([C:27]1([NH:26][C:25]([CH:9]2[NH:8][CH2:12][CH:11]([O:13][C:14](=[O:24])[C:15]3[CH:16]=[CH:17][C:18]([N+:21]([O-:23])=[O:22])=[CH:19][CH:20]=3)[CH2:10]2)=[O:37])[CH2:29][CH:28]1[CH:30]=[CH2:31])=[O:33])[CH3:36]

Participants

4

Reactant 1

HCID 668707382-(1-Ethoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-4-(4-nitro-benzoyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 668708334-Nitro-benzoic acid 5-(1-ethoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-pyrrolidin-3-yl esterYield 95.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 62406Trifluoromethanesulfonic acidSolvent

Procedure

Compound 133 (6.2 g, 12 mmol) was dissolved in an ice-cold mixture of trifluoro-methanesulfonic acid 33% in dichloromethane. The ice-bath was then removed and the mixture was left at room temperature for ˜1.5 h. The solvent was evaporated and 0.25 M sodium carbonate added and the mixture was extracted with dichloromethane. Evaporation gave the title compound (4.8 g, 95%) as a yellowish powder.

Workup

  1. customThe ice-bath was then removed
  2. customThe solvent was evaporated
  3. addition0.25 M sodium carbonate added
  4. extractionthe mixture was extracted with dichloromethane
  5. customEvaporation

Sources & evidence

ORD record
ord-1ef9eadfd3374796bd92aa07e265457c
Source dataset
uspto-grants-2014_06
Patent number
US08754106B2

Reaction notes

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