1,2,4-Triazole-1-acetic acid → (2S,4R)-1-(2-(1H-1,2,4-triazol-1-yl)acetyl)-N-(4-(4-fluorophenoxy)phenyl)-4-hydroxypyrrolidine-2-carboxamide

HRID 1630083Notes

Reaction equation

HRID 1630083 reaction equation
[N:1]1([CH2:6][C:7]([OH:9])=O)[CH:5]=[N:4][CH:3]=[N:2]1.[F:10][C:11]1[CH:39]=[CH:38][C:14]([O:15][C:16]2[CH:21]=[CH:20][C:19]([NH:22][C:23]([C@@H:25]3[CH2:29][C@@H:28]([OH:30])[CH2:27][N:26]3C(OC(C)(C)C)=O)=[O:24])=[CH:18][CH:17]=2)=[CH:13][CH:12]=1>>[N:1]1([CH2:6][C:7]([N:26]2[CH2:27][C@H:28]([OH:30])[CH2:29][C@H:25]2[C:23]([NH:22][C:19]2[CH:18]=[CH:17][C:16]([O:15][C:14]3[CH:38]=[CH:39][C:11]([F:10])=[CH:12][CH:13]=3)=[CH:21][CH:20]=2)=[O:24])=[O:9])[CH:5]=[N:4][CH:3]=[N:2]1

Participants

3

Reactant 2

HCID 18101801,2,4-Triazole-1-acetic acidHCID 67010572(2S,4R)-tert-butyl 2-(4-(4-fluorophenoxy)phenylcarbamoyl)-4-hydroxypyrrolidine-1-carboxylate

Product 1

HCID 56953686(2S,4R)-1-(2-(1H-1,2,4-triazol-1-yl)acetyl)-N-(4-(4-fluorophenoxy)phenyl)-4-hydroxypyrrolidine-2-carboxamide

Procedure

Proceeding as in Reference 11, but substituting 2-(1H-1,2,4-triazol-1-yl)acetic acid and (2S,4R)-tert-butyl 2-(4-(4-fluorophenoxy)phenylcarbamoyl)-4-hydroxypyrrolidine-1-carboxylate, gave (2S,4R)-1-(2-(1H-1,2,4-triazol-1-yl)acetyl)-N-(4-(4-fluorophenoxy)phenyl)-4-hydroxypyrrolidine-2-carboxamide.

Sources & evidence

ORD record
ord-ff95e7fdb8fc414d9f0228627ae47453
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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