1,2,4-Triazole-1-acetic acid → benzyl (3R,5S)-1-(2-(1H-1,2,4-triazol-1-yl)acetyl)-5-(4-(4-fluorophenoxy)phenylcarbamoyl)pyrrolidin-3-ylcarbamate

HRID 1630259Notes

Reaction equation

HRID 1630259 reaction equation
[F:1][C:2]1[CH:33]=[CH:32][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]([C@H:16]3[NH:20][CH2:19][C@H:18]([NH:21][C:22](=[O:31])[O:23][CH2:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH2:17]3)=[O:15])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[N:34]1([CH2:39][C:40](O)=[O:41])[CH:38]=[N:37][CH:36]=[N:35]1>>[N:34]1([CH2:39][C:40]([N:20]2[C@H:16]([C:14](=[O:15])[NH:13][C:10]3[CH:11]=[CH:12][C:7]([O:6][C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:33][CH:32]=4)=[CH:8][CH:9]=3)[CH2:17][C@@H:18]([NH:21][C:22](=[O:31])[O:23][CH2:24][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH2:19]2)=[O:41])[CH:38]=[N:37][CH:36]=[N:35]1

Participants

3

Reactant 2

HCID 18101801,2,4-Triazole-1-acetic acidHCID 68201126benzyl (3R,5S)-5-(4-(4-fluorophenoxy)phenylcarbamoyl)pyrrolidin-3-ylcarbamate

Product 1

HCID 86659490benzyl (3R,5S)-1-(2-(1H-1,2,4-triazol-1-yl)acetyl)-5-(4-(4-fluorophenoxy)phenylcarbamoyl)pyrrolidin-3-ylcarbamateYield 72%

Procedure

Proceeding as in Example 1, but substituting benzyl (3R,5S)-5-(4-(4-fluorophenoxy)phenylcarbamoyl)pyrrolidin-3-ylcarbamate and 2-(1H-1,2,4-triazol-1-yl)acetic acid, gave benzyl (3R,5S)-1-(2-(1H-1,2,4-triazol-1-yl)acetyl)-5-(4-(4-fluorophenoxy)phenylcarbamoyl)pyrrolidin-3-ylcarbamate (1.57 g, 2.81 mmol, 72% yield).

Sources & evidence

ORD record
ord-790e645bcd804c2e8f701e65e8c0f419
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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