Thioacetic acid → (2R,4S)-4-acetylthio-1-allyloxycarbonyl-2-[2-(2-hydroxymethylimidazol-1-yl) ethyl]pyrrolidine

HRID 975674Notes

Reaction equation

HRID 975674 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]=[CH:22][N:21]=[C:20]1[CH2:24][OH:25])=[O:6])[CH:2]=[CH2:3].[C:26]([SH:29])(=[O:28])[CH3:27]>>[C:26]([S:29][C@@H:10]1[CH2:11][N:7]([C:5]([O:4][CH2:1][CH:2]=[CH2:3])=[O:6])[C@H:8]([CH2:17][CH2:18][N:19]2[CH:23]=[CH:22][N:21]=[C:20]2[CH2:24][OH:25])[CH2:9]1)(=[O:28])[CH3:27]

Participants

3

Reactant 2

HCID 10484Thioacetic acidHCID 54269204(2R,4R)-1-allyloxycarbonyl-2-[2-(2-hydroxymethylimidazol-1-yl) ethyl]-4-methylsulfonyloxypyrrolidine

Product 1

HCID 57199532(2R,4S)-4-acetylthio-1-allyloxycarbonyl-2-[2-(2-hydroxymethylimidazol-1-yl) ethyl]pyrrolidine

Procedure

(2R,4R)-1-Allyloxycarbonyl-2-[2-(2-hydroxymethyl-imidazol-1-yl) ethyl]-4-methanesulfonyloxypyrrolidine (15.7 g) was reacted with thioacetic S-acid (6.30 ml) in substantially the same manner as that of Preparation 4-12) to give (2R,4S)-4-acetylthio-1-allyloxycarbonyl-2-[2-(2-hydroxymethylimidazol-1-yl) ethyl]pyrrolidine (5.93 g) as an orange paste.

Workup

  1. customof Preparation 4-12)

Sources & evidence

ORD record
ord-6a16eaf42b604cceade3e2c8d1f2577c
Source dataset
uspto-grants-1997_03
Patent number
US05608056

Reaction notes

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