(2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide → HCID 45377717, compound

HRID 1630211Notes

Reaction equation

HRID 1630211 reaction equation
Cl.[O:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[C:7]([OH:9])=O.[CH2:10]([C@H:17]1[CH2:21][NH:20][C@H:19]([C:22]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][C:32]3[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=3)=[CH:27][CH:26]=2)=[O:23])[CH2:18]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>>[CH2:10]([C@H:17]1[CH2:21][N:20]([C:7]([CH:3]2[CH2:4][CH2:5][CH2:6][O:2]2)=[O:9])[C@H:19]([C:22]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][C:32]3[CH:33]=[CH:34][C:35]([F:38])=[CH:36][CH:37]=3)=[CH:27][CH:26]=2)=[O:23])[CH2:18]1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

3

Reactant 2

HCID 67009148(2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamideHCID 67009570HCID 67009570, compound

Product 1

HCID 45377717HCID 45377717, compoundYield 33.4%

Procedure

Proceeding as in Example 1, but substituting tetrahydrofuran-2-carboxylic acid hydrochloride and (2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide, gave Compound 92, (2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)-1-(tetrahydrofuran-2-carbonyl)pyrrolidine-2-carboxamide (9.8 mg, 33.4%). Major isomer: 1H-NMR (400 MHz, DMSO-D6): a 9.97 (s, 1H), 7.54 (m, 2H), 7.27 (m, 2H), 7.21-7.15 (m, 7H), 6.93 (m, 2H), 4.55-4.43 (m, 2H), 3.73 (m, 2H), 2.64 (m, 3H), 2.03-1.90 (m, 4H), 1.86-1.76 (m, 4H). MS (EI) for C29H29FN2O4. found 489.5 (MH+).

Sources & evidence

ORD record
ord-ab870ec5751641c0b5455e9744791ada
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

Loading…