(2S,4R)-tert-butyl 4-(2-chlorophenylsulfonyl)-2-(1-cyanocyclopropylcarbamoyl)-pyrrolidine-1-carboxylate → (2S,4R)-4-(2-chlorophenylsulfonyl)-N-(1-cyanocyclopropyl)pyrrolidine-2-carboxamide

HRID 2403148Notes

Reaction equation

HRID 2403148 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([C@H:11]1[CH2:15][N:14](C(OC(C)(C)C)=O)[C@H:13]([C:23](=[O:30])[NH:24][C:25]2([C:28]#[N:29])[CH2:27][CH2:26]2)[CH2:12]1)(=[O:10])=[O:9]>C(O)=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([C@H:11]1[CH2:15][NH:14][C@H:13]([C:23]([NH:24][C:25]2([C:28]#[N:29])[CH2:27][CH2:26]2)=[O:30])[CH2:12]1)(=[O:10])=[O:9]

Participants

3

Reactant 1

HCID 66771127(2S,4R)-tert-butyl 4-(2-chlorophenylsulfonyl)-2-(1-cyanocyclopropylcarbamoyl)-pyrrolidine-1-carboxylate

Product 1

HCID 46946413(2S,4R)-4-(2-chlorophenylsulfonyl)-N-(1-cyanocyclopropyl)pyrrolidine-2-carboxamideYield 85%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

The reaction of the amide 6H with formic acid yielded (2S,4R)-4-(2-chlorophenylsulfonyl)-N-(1-cyanocyclopropyl)pyrrolidine-2-carboxamide as a white foam (85%). MS ISP (m/e): 354.2 (100) [(M+H)]+.

Sources & evidence

ORD record
ord-4c36f38f972c4920ac083827fc190e62
Source dataset
uspto-grants-2014_08
Patent number
US08802665B2

Reaction notes

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