(2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide → HCID 67009837, compound

HRID 1630217Notes

Reaction equation

HRID 1630217 reaction equation
Cl.[CH2:2]([O:4][CH2:5][CH2:6][C:7]([OH:9])=O)[CH3:3].[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](=[O:9])[CH2:6][CH2:5][O:4][CH2:2][CH3:3])[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 86659487HCID 86659487, compound

Product 1

HCID 67009837HCID 67009837, compoundYield 28.5%

Procedure

Proceeding as in Example 1, but substituting 3-ethoxypropanoic acid hydrochloride and (2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide, gave Compound 86, (2S,4R)-4-benzyl-1-(3-ethoxypropanoyl)-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide (8.4 mg, 28.5%). Major isomer: 1H-NMR (400 MHz, DMSO-D6): σ 9.91 (s, 1H), 7.55 (m, 2H), 7.28 (m, 2H), 7.21-7.16 (m, 7H), 6.93 (m, 2H), 4.45 (m, 1H), 3.64 (m, 1H), 3.54 (m, 2H), 3.38 (m, 2H), 3.24 (m, 1H), 2.63 (m, 5H), 1.88 (m, 2H), 1.04 (m, 3H). MS (EI) for C29H31FN2O4. found 491.6 (MH+).

Sources & evidence

ORD record
ord-7a9b3ce28c34408e9b2033e710e7a8bc
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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