(2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide → HCID 45377294, compound

HRID 1630228Notes

Reaction equation

HRID 1630228 reaction equation
Cl.[CH3:2][C:3]1[CH:7]=[C:6]([CH2:8][C:9]([OH:11])=O)[O:5][N:4]=1.[CH2:12]([C@H:19]1[CH2:23][NH:22][C@H:21]([C:24]([NH:26][C:27]2[CH:32]=[CH:31][C:30]([O:33][C:34]3[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=3)=[CH:29][CH:28]=2)=[O:25])[CH2:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[CH2:12]([C@H:19]1[CH2:23][N:22]([C:9](=[O:11])[CH2:8][C:6]2[O:5][N:4]=[C:3]([CH3:2])[CH:7]=2)[C@H:21]([C:24]([NH:26][C:27]2[CH:32]=[CH:31][C:30]([O:33][C:34]3[CH:35]=[CH:36][C:37]([F:40])=[CH:38][CH:39]=3)=[CH:29][CH:28]=2)=[O:25])[CH2:20]1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

3

Reactant 2

HCID 67009148(2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamideHCID 67010666(3-Methyl-isoxazol-5-yl)-acetic acid hydrochloride

Product 1

HCID 45377294HCID 45377294, compoundYield 29.2%

Procedure

Proceeding as in Example 1, but substituting 2-(3-methylisoxazol-5-yl)acetic acid hydrochloride and (2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide, gave Compound 32, (2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)-1-(2-(3-methylisoxazol-5-yl)acetyl)pyrrolidine-2-carboxamide (9 mg, 29.2%). 1H-NMR (400 MHz, DMSO-D6): σ 9.97 (s, 1H), 7.54 (d, 2H), 7.27 (t, 2H), 7.19 (m, 4H), 6.67 (m, 4H), 6.20 (d, 1H), 4.48 (1H), 3.88 (m, 3H), 2.66 (m, 4H), 2.15 (s, 3H), 1.91 (m, 2H). MS (EI) for C30H28FN3O4: 514.6 (MH+).

Sources & evidence

ORD record
ord-45d23f1f46644bacb4ed4a415ec8b343
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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