Potassium tert-butoxide → (2R,4S)-1-allyloxycarbonyl-4-acetylthio-2-[2-(4-cyanoimidazol-1-yl)ethyl]pyrrolidine

HRID 975711Notes

Reaction equation

HRID 975711 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10](OS(C)(=O)=O)[CH2:9][C@H:8]1[CH2:17][CH2:18][N:19]1[CH:23]=[C:22]([C:24]#[N:25])[N:21]=[CH:20]1)=[O:6])[CH:2]=[CH2:3].[C:26]([OH:29])(=[S:28])[CH3:27].CC(C)([O-])C.[K+]>>[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@@H:10]([S:28][C:26](=[O:29])[CH3:27])[CH2:9][C@H:8]1[CH2:17][CH2:18][N:19]1[CH:23]=[C:22]([C:24]#[N:25])[N:21]=[CH:20]1)=[O:6])[CH:2]=[CH2:3]

Participants

4

Reactant 3

HCID 23665647Potassium tert-butoxideHCID 53735347(2R,4R)-1-Allyloxycarbonyl-2-[2-(4-cyanoimidazol-1-yl) ethyl]-4-methanesulfonyloxypyrrolidineHCID 178418634HCID 178418634, compound

Product 1

HCID 53670605(2R,4S)-1-allyloxycarbonyl-4-acetylthio-2-[2-(4-cyanoimidazol-1-yl)ethyl]pyrrolidine

Procedure

(2R,4R)-1-Allyloxycarbonyl-2-[2-(4-cyanoimidazol-1-yl) ethyl]-4-methanesulfonyloxypyrrolidine (13.4 g) was reacted with thioacetic acid (5.46 ml) and potassium t-butoxide (8.17 g) in substantially the same manner as Preparation 4-12) to give (2R,4S)-1-allyloxycarbonyl-4-acetylthio-2-[2-(4-cyanoimidazol-1-yl)ethyl]pyrrolidine (12.5 g) as a yellow paste.

Workup

  1. customas Preparation 4-12)

Sources & evidence

ORD record
ord-e16d1bd705874bac95da9d1443059454
Source dataset
uspto-grants-1997_03
Patent number
US05608056

Reaction notes

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