Potassium tert-butoxide → (2R,4S)-1-allyloxycarbonyl-4-acetylthio-2-[2-(5-hydroxymethyl-imidazol-1-yl)ethyl]pyrrolidine

HRID 975709Notes

Reaction equation

HRID 975709 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[C:23]([CH2:24][OH:25])=[CH:22][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[C:23]([CH2:24][OH:25])=[CH:22][N:21]=[CH:20]1)=[O:6])[CH:2]=[CH2:3]

Participants

4

Reactant 3

HCID 23665647Potassium tert-butoxideHCID 54381297(2R,4R)-1-Allyloxycarbonyl-2-[2-(5-hydroxymethyl-imidazol-1-yl) ethyl]-4-methanesulfonyloxypyrrolidineHCID 178418634HCID 178418634, compound

Product 1

HCID 54235556(2R,4S)-1-allyloxycarbonyl-4-acetylthio-2-[2-(5-hydroxymethyl-imidazol-1-yl)ethyl]pyrrolidine

Procedure

(2R,4R)-1-Allyloxycarbonyl-2-[2-(5-hydroxymethyl-imidazol-1-yl) ethyl]-4-methanesulfonyloxypyrrolidine (1.63 g) was reacted with thioacetic acid (0.65 ml) and potassium t-butoxide (0.978 g) in substantially the same manner as that of Preparation 14-12) to give (2R,4S)-1-allyloxycarbonyl-4-acetylthio-2-[2-(5-hydroxymethyl-imidazol-1-yl)ethyl]pyrrolidine (884 mg) as an orange paste.

Workup

  1. customof Preparation 14-12)

Sources & evidence

ORD record
ord-7736ba359999432b899d01723d223ac4
Source dataset
uspto-grants-1997_03
Patent number
US05608056

Reaction notes

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