(2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide → HCID 67010822, compound

HRID 1630218Notes

Reaction equation

HRID 1630218 reaction equation
Cl.[CH3:2][S: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][S: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 86659488HCID 86659488, compound

Product 1

HCID 67010822HCID 67010822, compoundYield 28.1%

Procedure

Proceeding as in Example 1, but substituting 3-(methylthio)propanoic acid hydrochloride and (2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide, gave Compound 85, (2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)-1-(3-(methylthio)propanoyl)pyrrolidine-2-carboxamide (8.3 mg, 28.1%). Major isomer: 1H-NMR (400 MHz, DMSO-D6): σ 9.91 (s, 1H), 7.54 (d, 2H), 7.27 (m, 2H), 7.22-7.15 (m, 7H), 6.93 (m, 2H), 4.46 (t, 1H), 3.66 (m, 1H), 3.23 (m, 1H), 2.65-2.59 (m, 6H), 2.56 (m, 1H), 2.04 (s, 3H), 1.90 (m, 2H). MS (EI) for C28H29FN2O3S: 493.6 (MH+).

Sources & evidence

ORD record
ord-d164c076af9d4711bab418c6af887f5e
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

Loading…