Imidazolecarboxamide → (2R,4R)-1-allyloxycarbonyl-2-{2-(2-carbamoylimidazol-1-yl) ethyl}-4-methylsulfonyloxypyrrolidine

HRID 975675Notes

Reaction equation

HRID 975675 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10]([O:12][S:13]([CH3:16])(=[O:15])=[O:14])[CH2:9][C@H:8]1[CH2:17][CH2:18]OS(C)(=O)=O)=[O:6])[CH:2]=[CH2:3].[C:24]([C:27]1[NH:28][CH:29]=[CH:30][N:31]=1)(=[O:26])[NH2:25]>>[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10]([O:12][S:13]([CH3:16])(=[O:14])=[O:15])[CH2:9][C@H:8]1[CH2:17][CH2:18][N:28]1[CH:29]=[CH:30][N:31]=[C:27]1[C:24](=[O:26])[NH2:25])=[O:6])[CH:2]=[CH2:3]

Participants

3

Reactant 2

HCID 133520ImidazolecarboxamideHCID 15537962(2R,4R)-1-Allyloxycarbonyl-4-methylsulfonyloxy-2-(2-methylsulfonyloxyethyl) pyrrolidine

Product 1

HCID 54523979(2R,4R)-1-allyloxycarbonyl-2-{2-(2-carbamoylimidazol-1-yl) ethyl}-4-methylsulfonyloxypyrrolidineYield 68%

Procedure

(2R,4R)-1-Allyloxycarbonyl-4-methylsulfonyloxy-2-(2-methylsulfonyloxyethyl) pyrrolidine (21.5 g) and 2-carbamoylimidazole (7.07 g) were reacted in substantially the same manner as that of Preparation 10-3) to give (2R,4R)-1-allyloxycarbonyl-2-{2-(2-carbamoylimidazol-1-yl) ethyl}-4-methylsulfonyloxypyrrolidine (15.2 g) as a yellow solid.

Workup

  1. customof Preparation 10-3)

Sources & evidence

ORD record
ord-199d164aaab047208989b6c739204157
Source dataset
uspto-grants-1997_03
Patent number
US05608056

Reaction notes

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