(2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide → HCID 67009396, compound

HRID 1630216Notes

Reaction equation

HRID 1630216 reaction equation
Cl.[CH3:2][S:3]([CH2:6][C:7]([OH:9])=O)(=[O:5])=[O:4].[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][S:3]([CH3:2])(=[O:5])=[O:4])[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 86659486HCID 86659486, compound

Product 1

HCID 67009396HCID 67009396, compoundYield 24.8%

Procedure

Proceeding as in Example 1, but substituting 2-(methylsulfonyl)acetic acid hydrochloride and (2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide, gave Compound 87, (2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)-1-(2-(methylsulfonyl)acetyl)pyrrolidine-2-carboxamide (7.6 mg, 24.8%). Major isomer: 1H-NMR (400 MHz, DMSO-D6): σ 9.96 (s, 1H), 7.55 (m, 2H), 7.27 (m, 2H), 7.23-7.16 (m, 7H), 6.94 (m, 2H), 4.50 (m, 1H), 4.38 (d, 2H), 3.82 (m, 1H), 3.35 (m, 1H), 3.08 (s, 3H), 2.63 (m, 3H), 1.92 (m, 2H). MS (EI) for C27H27FN2O5S. found 511.6 (MH+).

Sources & evidence

ORD record
ord-1266ec0800514980be037f7b8a001b08
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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