(2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide → HCID 67009861, compound

HRID 1630213Notes

Reaction equation

HRID 1630213 reaction equation
Cl.[CH3:2][O:3][CH2:4][CH2:5][C:6]([OH:8])=O.[CH2:9]([C@H:16]1[CH2:20][NH:19][C@H:18]([C:21]([NH:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][C:31]3[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=3)=[CH:26][CH:25]=2)=[O:22])[CH2:17]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>>[CH2:9]([C@H:16]1[CH2:20][N:19]([C:6](=[O:8])[CH2:5][CH2:4][O:3][CH3:2])[C@H:18]([C:21]([NH:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][C:31]3[CH:32]=[CH:33][C:34]([F:37])=[CH:35][CH:36]=3)=[CH:26][CH:25]=2)=[O:22])[CH2:17]1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

3

Reactant 2

HCID 67009148(2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamideHCID 86659483HCID 86659483, compound

Product 1

HCID 67009861HCID 67009861, compoundYield 24.1%

Procedure

Proceeding as in Example 1, but substituting 3-methoxypropanoic acid hydrochloride and (2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide, gave Compound 90, (2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)-1-(3-methoxypropanoyl)pyrrolidine-2-carboxamide (6.9 mg, 24.1%). Major isomer: 1H-NMR (400 MHz, DMSO-D6): 9.90 (s, 1H), 7.54 (m, 2H), 7.30-7.25 (m, 3H), 7.21-7.16 (m, 6H), 6.92 (m, 2H), 4.44 (m, 1H), 3.66 (m, 1H), 3.51 (m, 3H), 3.19 (s, 3H), 2.63 (m, 4H), 2.09 (m, 1H), 1.88 (m, 2H). MS (EI) for C28H29FN2O4. found 477.5 (MH+).

Sources & evidence

ORD record
ord-1c65eb58d7dc42d5973c5215680d9c66
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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