(2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide → HCID 67010817, compound

HRID 1630221Notes

Reaction equation

HRID 1630221 reaction equation
Cl.[O:2]=[C:3]1[O:7][C@H:6]([C:8]([OH:10])=O)[CH2:5][CH2:4]1.[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]([C@@H:6]2[CH2:5][CH2:4][C:3](=[O:2])[O:7]2)=[O:10])[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 67009428HCID 67009428, compound

Product 1

HCID 67010817HCID 67010817, compoundYield 29.2%

Procedure

Proceeding as in Example 1, but substituting (S)-5-oxotetrahydrofuran-2-carboxylic acid hydrochloride and (2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide, gave Compound 39, (2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)-1-((S)-5-oxotetrahydrofuran-2-carbonyl)pyrrolidine-2-carboxamide (8.8 mg, 29.2%). 1H-NMR (400 MHz, DMSO-D6): σ 10.04 (s, 1H), 7.53 (m, 2H), 7.27 (m, 2H), 7.18 (m, 5H), 6.94 (m, 4H), 5.28 (m, 1H), 4.52 (dd, 1H), 3.65 (m, 1H), 2.39 (m, 3H), 2.46 (m, 3H), 2.15 (m, 2H), 2.89 (m, 2H). MS (EI) for C29H27FN2O5: 503.5 (MH+).

Sources & evidence

ORD record
ord-71ef7fa4ac4c4ce5afdbd93e8ebc0c7d
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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