(2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide → (2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)-1-(4-oxo-4-phenylbutanoyl)pyrrolidine-2-carboxamide

HRID 1630196Notes

Reaction equation

HRID 1630196 reaction equation
Cl.[O:2]=[C:3]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:4][CH2:5][C:6]([OH:8])=O.[CH2:15]([C@H:22]1[CH2:26][NH:25][C@H:24]([C:27]([NH:29][C:30]2[CH:35]=[CH:34][C:33]([O:36][C:37]3[CH:42]=[CH:41][C:40]([F:43])=[CH:39][CH:38]=3)=[CH:32][CH:31]=2)=[O:28])[CH2:23]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>>[CH2:15]([C@H:22]1[CH2:26][N:25]([C:6](=[O:8])[CH2:5][CH2:4][C:3](=[O:2])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C@H:24]([C:27]([NH:29][C:30]2[CH:35]=[CH:34][C:33]([O:36][C:37]3[CH:38]=[CH:39][C:40]([F:43])=[CH:41][CH:42]=3)=[CH:32][CH:31]=2)=[O:28])[CH2:23]1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

3

Reactant 2

HCID 67009148(2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamideHCID 670095694-Oxo-4-phenylbutanoic acid hydrochloride

Product 1

HCID 45377859(2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)-1-(4-oxo-4-phenylbutanoyl)pyrrolidine-2-carboxamideYield 39.7%

Procedure

Proceeding as in Example 1, but substituting 4-oxo-4-phenylbutanoic acid hydrochloride and (2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide, gave Compound 124, (2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)-1-(4-oxo-4-phenylbutanoyl)pyrrolidine-2-carboxamide (13.1 mg, 39.7%); Major isomer: 1H-NMR (400 MHz, DMSO-D6): σ 9.87 (s, 1H), 7.94-7.99 (m, 2H), 7.60-7.605 (m, 2H), 7.50-7.56 (m, 3H), 7.30-7.34 (m, 2H), 7.17-7.23 (m, 5H), 6.95-7.02 (m, 4H), 4.46 (m, 1H), 3.73 (m, 1H), 3.28 (m, 4H), 3.13 (m, 1H), 2.66 (m, 3H), 1.93 (m, 2H). MS (EI) for C34H31FN2O4. found 551.6 (MH+).

Sources & evidence

ORD record
ord-f6e7e4b3a09e4078a3407606213c8e23
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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