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 390126Notes

Reaction equation

HRID 390126 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>C(O)(C(F)(F)F)=O.C(Cl)Cl>[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 98%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

Compound 21b (11.84 g, 22.9 mmol) was deprotected in TFA (30 ml) dissolved in DCM (100 ml) and then worked up by methods known in the chemical art to give the title compound (9.37 g, 98%).

Sources & evidence

ORD record
ord-762d5fe35ed144baa17a05e0d985886a
Source dataset
uspto-grants-2013_02
Patent number
US08383584B2

Reaction notes

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