(2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide → methyl 4-((2S,4R)-4-benzyl-2-(4-(4-fluorophenoxy)phenylcarbamoyl)pyrrolidin-1-yl)-4-oxobutanoate

HRID 1630195Notes

Reaction equation

HRID 1630195 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:10])[CH2:5][CH2:6][C:7]([OH:9])=O.[CH2:11]([C@H:18]1[CH2:22][NH:21][C@H:20]([C:23]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([O:32][C:33]3[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=3)=[CH:28][CH:27]=2)=[O:24])[CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[CH2:11]([C@H:18]1[CH2:22][N:21]([C:7](=[O:9])[CH2:6][CH2:5][C:4]([O:3][CH3:2])=[O:10])[C@H:20]([C:23](=[O:24])[NH:25][C:26]2[CH:31]=[CH:30][C:29]([O:32][C:33]3[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=3)=[CH:28][CH:27]=2)[CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

3

Reactant 2

HCID 67009148(2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamideHCID 866594764-Methoxy-4-oxobutanoic acid hydrochloride

Product 1

HCID 67009301methyl 4-((2S,4R)-4-benzyl-2-(4-(4-fluorophenoxy)phenylcarbamoyl)pyrrolidin-1-yl)-4-oxobutanoateYield 27.4%

Procedure

Proceeding as in Example 1, but substituting 4-methoxy-4-oxobutanoic acid hydrochloride and (2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide, gave Compound 125, methyl 4-((2S,4R)-4-benzyl-2-(4-(4-fluorophenoxy)phenylcarbamoyl)pyrrolidin-1-yl)-4-oxobutanoate (8.3 mg, 27.4%); Major isomer: 1H-NMR (400 MHz, DMSO-D6): σ 9.90 (s, 1H), 7.54-7.60 (m, 2H), 7.28-7.32 (m, 2H), 7.16-7.24 (m, 5H), 6.93-7.02 (m, 4H), 4.45 (m, 1H), 3.64-3.68 (m, 1H), 3.57 (s, 3H), 3.10-3.11 (m, 1H), 2.66 (m, 2H), 2.54 (m, 2H), 2.47 (m, 2H), 19.2 (m, 2H). MS (EI) for C29H29FN2O5. found 505.5 (MH+).

Sources & evidence

ORD record
ord-669e3407a7984c428a36453f5ed41876
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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