(2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide → HCID 67009600, compound

HRID 1630212Notes

Reaction equation

HRID 1630212 reaction equation
Cl.[O:2]=[C:3]([C:9]1[S:10][CH:11]=[CH:12][CH:13]=1)[CH2:4][CH2:5][C:6]([OH:8])=O.[CH2:14]([C@H:21]1[CH2:25][NH:24][C@H:23]([C:26]([NH:28][C:29]2[CH:34]=[CH:33][C:32]([O:35][C:36]3[CH:41]=[CH:40][C:39]([F:42])=[CH:38][CH:37]=3)=[CH:31][CH:30]=2)=[O:27])[CH2:22]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[CH2:14]([C@H:21]1[CH2:25][N:24]([C:6](=[O:8])[CH2:5][CH2:4][C:3](=[O:2])[C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)[C@H:23]([C:26]([NH:28][C:29]2[CH:34]=[CH:33][C:32]([O:35][C:36]3[CH:37]=[CH:38][C:39]([F:42])=[CH:40][CH:41]=3)=[CH:31][CH:30]=2)=[O:27])[CH2:22]1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

3

Reactant 2

HCID 67009148(2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamideHCID 67009875HCID 67009875, compound

Product 1

HCID 67009600HCID 67009600, compoundYield 32.3%

Procedure

Proceeding as in Example 1, but substituting 4-oxo-4-(thien-2-yl)butanoic acid hydrochloride and (2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide, gave Compound 91, (2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)-1-(4-oxo-4-(thien-2-yl)butanoyl)pyrrolidine-2-carboxamide (10.8 mg, 32.3%). Major isomer: 1H-NMR (400 MHz, DMSO-D6): a 9.84 (s, 1H), 7.95 (m, 2H), 7.53 (m, 2H), 7.29 (m, 2H), 7.24-7.14 (m, 8H), 6.91 (m, 2H), 4.43 (t, 1H), 3.69 (m, 1H), 3.24 (m, 1H), 3.05 (m, 2H), 2.67-2.59 (m, 5H), 1.91 (m, 2H). MS (EI) for C32H29FN2O4S. found 557.7 (MH+).

Sources & evidence

ORD record
ord-2eeac33f7f2e4aeb91d30a4ac01a875f
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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