(2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide → HCID 86659481, compound

HRID 1630204Notes

Reaction equation

HRID 1630204 reaction equation
Cl.[O:2]=[C:3]1[CH2:7][S:6][C:5](=[S:8])[N:4]1[CH2:9][C:10]([OH:12])=O.[CH2:13]([C@H:20]1[CH2:24][NH:23][C@H:22]([C:25]([NH:27][C:28]2[CH:33]=[CH:32][C:31]([O:34][C:35]3[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH:36]=3)=[CH:30][CH:29]=2)=[O:26])[CH2:21]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[CH2:13]([C@H:20]1[CH2:24][N:23]([C:10](=[O:12])[CH2:9][N:4]2[C:3](=[O:2])[CH2:7][S:6][C:5]2=[S:8])[C@H:22]([C:25]([NH:27][C:28]2[CH:33]=[CH:32][C:31]([O:34][C:35]3[CH:36]=[CH:37][C:38]([F:41])=[CH:39][CH:40]=3)=[CH:30][CH:29]=2)=[O:26])[CH2:21]1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

3

Reactant 2

HCID 67009148(2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamideHCID 86659482HCID 86659482, compound

Product 1

HCID 86659481HCID 86659481, compoundYield 39.9%

Procedure

Proceeding as in Example 1, but substituting 2-(4-oxo-2-thioxothiazolidin-3-yl)acetic acid hydrochloride and (2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide, gave Compound 99, (2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)-1-(2-(4-oxo-2-thioxothiazolidin-3-yl)acetyl)pyrrolidine-2-carboxamide (13.5 mg, 39.9%). Major isomer: 1H-NMR (400 MHz, DMSO-D6): σ 9.92 (s, 1H), 7.51 (d, 2H), 7.30-7.16 (m, 9H), 6.93 (m, 2H), 4.76 (m, 1H), 4.60 (m, 1H), 4.43 (m, 1H), 4.35 (m, 2H), 2.87 (s, 2H), 2.68 (m, 3H), 1.95 (m, 2H). MS (EI) for C29H26FN3O4S2. found 564.7 (MH+).

Sources & evidence

ORD record
ord-56e2128697a647caa8870bfeb3da645b
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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