(2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide → HCID 67010754, compound

HRID 1630199Notes

Reaction equation

HRID 1630199 reaction equation
Cl.[CH2:2]([O:4][CH2:5][C:6]([OH:8])=O)[CH3:3].[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][O:4][CH2:2][CH3:3])[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 86659478HCID 86659478, compound

Product 1

HCID 67010754HCID 67010754, compoundYield 32.9%

Procedure

Proceeding as in Example 1, but substituting 2-ethoxyacetic acid hydrochloride and (2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide, gave Compound 121, (2S,4R)-4-benzyl-1-(2-ethoxyacetyl)-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide (9.4 mg, 32.9%); Major isomer: 1H-NMR (400 MHz, DMSO-D6): σ 9.99 (s, 1H), 7.55-7.60 (m, 2H), 7.29-7.32 (m, 2H), 7.17-7.23 (m, 5H), 6.95-7.02 (m, 4H), 4.47 (m, 1H), 4.06 (d, 2H), 3.60-3.64 (m, 1H), 3.47-3.53 (m, 2H), 3.18-3.22 (m, 1H), 2.50-2.89 (m, 3H), 1.90 (m, 2H), 1.08 (m, 3H). MS (EI) for C28H29FN2O4. found 477.5 (MH+).

Sources & evidence

ORD record
ord-26cc25f567be4d6595ed2db3ccf96ecc
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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