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

HRID 2403149Notes

Reaction equation

HRID 2403149 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[S:9][C@H:10]1[CH2:14][N:13](C(OC(C)(C)C)=O)[C@H:12]([C:22](=[O:29])[NH:23][C:24]2([C:27]#[N:28])[CH2:26][CH2:25]2)[CH2:11]1>C(O)=O>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[S:9][C@H:10]1[CH2:14][NH:13][C@H:12]([C:22]([NH:23][C:24]2([C:27]#[N:28])[CH2:26][CH2:25]2)=[O:29])[CH2:11]1

Participants

3

Reactant 1

HCID 86692744(2S,4R)-tert-butyl 4-(2-chloro-4-fluorophenylthio)-2-(1-cyanocyclopropylcarbamoyl)pyrrolidine-1-carboxylate

Product 1

HCID 86692743(2S,4R)-4-(2-chloro-4-fluorophenylthio)-N-(1-cyanocyclopropyl)pyrrolidine-2-carboxamideYield 99%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

The reaction of the amide 11A with formic acid yielded (2S,4R)-4-(2-chloro-4-fluorophenylthio)-N-(1-cyanocyclopropyl)pyrrolidine-2-carboxamide as a light yellow viscous oil (99%). MS ISP (m/e): 340.2/342.0 (100/25) [(M+H)]+, 230.2/232.0 (94/40).

Sources & evidence

ORD record
ord-978bdaeac6154365bbd88e20796fba5b
Source dataset
uspto-grants-2014_08
Patent number
US08802665B2

Reaction notes

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