(2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide → HCID 45377583, compound

HRID 1630215Notes

Reaction equation

HRID 1630215 reaction equation
Cl.[CH3:2][O:3][CH2:4][CH2:5][O:6][CH2:7][C:8]([OH:10])=O.[CH2:11]([C@H:18]1[CH2:22][NH:21][C@H:20]([C:23]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([O:32][C:33]3[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=3)=[CH:28][CH:27]=2)=[O:24])[CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[CH2:11]([C@H:18]1[CH2:22][N:21]([C:8](=[O:10])[CH2:7][O:6][CH2:5][CH2:4][O:3][CH3:2])[C@H:20]([C:23]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([O:32][C:33]3[CH:34]=[CH:35][C:36]([F:39])=[CH:37][CH:38]=3)=[CH:28][CH:27]=2)=[O:24])[CH2:19]1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

3

Reactant 2

HCID 67009148(2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamideHCID 86659485HCID 86659485, compound

Product 1

HCID 45377583HCID 45377583, compoundYield 26.6%

Procedure

Proceeding as in Example 1, but substituting 2-(2-methoxyethoxy)acetic acid hydrochloride and (2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide, gave Compound 88, (2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)-1-(2-(2-methoxyethoxy)acetyl)pyrrolidine-2-carboxamide (8.1 mg, 26.6%). Major isomer: 1H-NMR (400 MHz, DMSO-D6): a 9.95 (s, 1H), 7.54 (m, 2H), 7.27 (m, 2H), 7.21-7.15 (m, 7H), 6.93 (m, 2H), 4.47 (m, 1H), 4.08 (m, 2H), 3.62-3.42 (m, 6H), 3.21 (s, 3H), 2.63 (m, 3H), 1.88 (m, 2H). MS (EI) for C29H31FN2O5. found 507.6 (MH+).

Sources & evidence

ORD record
ord-f605d25c701b4b5498ea983d36a3109e
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

Loading…