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

HRID 2403151Notes

Reaction equation

HRID 2403151 reaction equation
[C:1]([C:3]1([NH:6][C:7]([C@@H:9]2[CH2:13][C@@H:12]([S:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[O:21][C:22]([F:25])([F:24])[F:23])[CH2:11][N:10]2C(OC(C)(C)C)=O)=[O:8])[CH2:5][CH2:4]1)#[N:2]>C(O)=O>[C:1]([C:3]1([NH:6][C:7]([C@@H:9]2[CH2:13][C@@H:12]([S:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[O:21][C:22]([F:25])([F:23])[F:24])[CH2:11][NH:10]2)=[O:8])[CH2:4][CH2:5]1)#[N:2]

Participants

3

Reactant 1

HCID 67278971(2S,4R)-tert-butyl 2-(1-cyanocyclopropylcarbamoyl)-4-(2-(trifluoromethoxy)phenylthio)pyrrolidine-1-carboxylate

Product 1

HCID 86692747(2S,4R)-N-(1-cyanocyclopropyl)-4-(2-(trifluoromethoxy)phenylthio)pyrrolidine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

The reaction of the amide 11D with formic acid yielded (2S,4R)-N-(1-cyanocyclopropyl)-4-(2-(trifluoromethoxy)phenylthio)pyrrolidine-2-carboxamide as a colorless viscous oil (quant.). MS ISP (m/e): 372.1 (94) [(M+H)]+, 262.1 (100).

Sources & evidence

ORD record
ord-2cce966608fc4c6897ae214078d0f550
Source dataset
uspto-grants-2014_08
Patent number
US08802665B2

Reaction notes

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