Benzyl mercaptan → (2S,4R)-4-(benzylthio)-1-(1-(4-chlorophenyl)cyclopropanecarbonyl)-N-(1-cyanocyclopropyl)pyrrolidine-2-carboxamide

HRID 1697734Notes

Reaction equation

C1(S(O[C@H:11]2[CH2:15][C@@H:14]([C:16](=[O:23])[NH:17][C:18]3([C:21]#[N:22])[CH2:20][CH2:19]3)[N:13]([C:24]([C:26]3([C:29]4[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=4)[CH2:28][CH2:27]3)=[O:25])[CH2:12]2)(=O)=O)C=CC=CC=1.[C:36]1([CH2:42][SH:43])[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>>[CH2:42]([S:43][C@H:11]1[CH2:12][N:13]([C:24]([C:26]2([C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=3)[CH2:27][CH2:28]2)=[O:25])[C@H:14]([C:16]([NH:17][C:18]2([C:21]#[N:22])[CH2:19][CH2:20]2)=[O:23])[CH2:15]1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

Reactant 2

HCID 7509Benzyl mercaptan

HCID 86646867(3S,5S)-1-(1-(4-chlorophenyl)cyclopropanecarbonyl)-5-(1-cyanocyclopropylcarbamoyl)pyrrolidin-3-yl Benzenesulfonate

Product 1

HCID 66772557(2S,4R)-4-(benzylthio)-1-(1-(4-chlorophenyl)cyclopropanecarbonyl)-N-(1-cyanocyclopropyl)pyrrolidine-2-carboxamide

Procedure

The title compound was prepared in analogy to example 457d) using (3S,5S)-1-(1-(4-chlorophenyl)cyclopropanecarbonyl)-5-(1-cyanocyclopropylcarbamoyl)pyrrolidin-3-yl benzenesulfonate (example 457, step 3; 200 mg) and phenylmethanethiol (57 mg) to yield 109 mg (53%) of a white solid. MS (ESI): m/z=480.15 [M−H]+.

Sources & evidence

ORD record: ord-ea57b7308560496cb32e8bb1a18d7c35
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163793B2

Reaction notes

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