(2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide → HCID 45377858, compound

HRID 1630200Notes

Reaction equation

HRID 1630200 reaction equation
Cl.[OH:2][CH2:3][C:4]([OH:6])=O.[CH2:7]([C@H:14]1[CH2:18][NH:17][C@H:16]([C:19]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=3)=[CH:24][CH:23]=2)=[O:20])[CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>>[CH2:7]([C@H:14]1[CH2:18][N:17]([C:4](=[O:6])[CH2:3][OH:2])[C@H:16]([C:19]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][C:29]3[CH:30]=[CH:31][C:32]([F:35])=[CH:33][CH:34]=3)=[CH:24][CH:23]=2)=[O:20])[CH2:15]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

3

Reactant 2

HCID 67009148(2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamideHCID 86659479HCID 86659479, compound

Product 1

HCID 45377858HCID 45377858, compoundYield 33.8%

Procedure

Proceeding as in Example 1, but substituting 2-hydroxyacetic acid hydrochloride and (2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide, gave Compound 120, (2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)-1-(2-hydroxyacetyl)pyrrolidine-2-carboxamide (9.1 mg, 33.8%); Major isomer: 1H-NMR (400 MHz, DMSO-D6): σ 9.97 (s, 1H), 7.55-7.59 (m, 2H), 7.28-7.32 (m, 2H), 7.17-7.23 (m, 5H), 6.94-7.02 (m, 4H), 4.50-4.52 (m, 1H), 4.02 (s, 2H), 3.50-3.59 (m, 1H), 3.15 (m, 1H), 2.63-2.73 (m, 3H), 1.89-1.93 (m, 2H). MS (EI) for C26H25FN2O4. found 449.4 (MH+).

Sources & evidence

ORD record
ord-5f2ba6daaf2a488981a3941b344fcb05
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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