(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid → (2S,4R)-tert-butyl 2-(4-(4-fluorophenoxy)phenylcarbamoyl)-4-hydroxypyrrolidine-1-carboxylate

HRID 1630065Notes

Reaction equation

HRID 1630065 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([OH:13])[CH2:10][C@H:9]1[C:14]([OH:16])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:17][C:18]1[CH:31]=[CH:30][C:21]([O:22][C:23]2[CH:29]=[CH:28][C:26]([NH2:27])=[CH:25][CH:24]=2)=[CH:20][CH:19]=1>>[F:17][C:18]1[CH:31]=[CH:30][C:21]([O:22][C:23]2[CH:29]=[CH:28][C:26]([NH:27][C:14]([C@@H:9]3[CH2:10][C@@H:11]([OH:13])[CH2:12][N:8]3[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[O:16])=[CH:25][CH:24]=2)=[CH:20][CH:19]=1

Participants

3

Reactant 2

HCID 88804(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acidHCID 147633Benzenamine, 4-(4-fluorophenoxy)-

Product 1

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

Procedure

Proceeding as in Reference 5, but substituting (2S,4R)-1-(tert-butoxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid and 4-(4-fluorophenoxy)aniline, gave (2S,4R)-tert-butyl 2-(4-(4-fluorophenoxy)phenylcarbamoyl)-4-hydroxypyrrolidine-1-carboxylate.

Sources & evidence

ORD record
ord-cfd4a7812a6f4e7dae527b2a218b2356
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

Loading…