(2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide → HCID 67010173, compound

HRID 1630202Notes

Reaction equation

HRID 1630202 reaction equation
Cl.[OH:2][CH:3]([CH3:8])[CH2:4][C:5]([OH:7])=O.[CH2:9]([C@H:16]1[CH2:20][NH:19][C@H:18]([C:21]([NH:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][C:31]3[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=3)=[CH:26][CH:25]=2)=[O:22])[CH2:17]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>>[CH2:9]([C@H:16]1[CH2:20][N:19]([C:5](=[O:7])[CH2:4][CH:3]([OH:2])[CH3:8])[C@H:18]([C:21]([NH:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][C:31]3[CH:32]=[CH:33][C:34]([F:37])=[CH:35][CH:36]=3)=[CH:26][CH:25]=2)=[O:22])[CH2:17]1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

3

Reactant 2

HCID 67009148(2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamideHCID 86659480HCID 86659480, compound

Product 1

HCID 67010173HCID 67010173, compoundYield 29.7%

Procedure

Proceeding as in Example 1, but substituting 3-hydroxybutanoic acid hydrochloride and (2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide, gave Compound 118, (2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)-1-(3-hydroxybutanoyl)pyrrolidine-2-carboxamide (8.5 mg, 29.7%); Major isomer: 1H-NMR (400 MHz, DMSO-D6): σ 9.93 (s, 1H), 7.55-7.60 (m, 2H), 7.28-7.35 (m, 2H), 7.17-7.24 (m, 5H), 6.94-7.02 (m, 4H), 4.67 (m, 1H), 4.47-4.50 (m, 1H), 3.90 (m, 1H), 3.68-3.70 (m, 1H), 3.25-3.30 (m, 1H), 2.63-2.73 (m, 3H), 2.35-2.47 (m, 1H), 2.70-2.30 (m, 1H), 1.86-1.96 (m, 2H), 1.01-1.13 (m, 3H). MS (EI) for C28H29FN2O4. found 477.5 (MH+).

Sources & evidence

ORD record
ord-822d0b7f9c674d5eb72b3d99572dc7bf
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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