3,3,3-Trifluoropropionic acid → HCID 67009871, compound

HRID 1630226Notes

Reaction equation

HRID 1630226 reaction equation
[F:1][C:2]([F:8])([F:7])[CH2:3][C:4](O)=[O:5].[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:4](=[O:5])[CH2:3][C:2]([F:8])([F:7])[F:1])[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 27779723,3,3-Trifluoropropionic acidHCID 67009148(2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide

Product 1

HCID 67009871HCID 67009871, compoundYield 30.6%

Procedure

Proceeding as in Example 1, but substituting 3,3,3-trifluoropropanoic acid and (2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide, gave Compound 34, (2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)-1-(3,3,3-trifluoropropanoyl)pyrrolidine-2-carboxamide (9.2 mg, 30.6%). 1H-NMR (400 MHz, DMSO-D6): σ 9.98 (s, 1H), 7.54 (m, 2H), 7.22 (m, 2H), 7.17 (m, 5H), 6.93 (m, 4H), 4.49 (m, 1H), 3.60 (m, 2H), 3.26 (m, 1H), 2.65 (m, 3H), 1.91 (m, 2H). MS (EI) for C27H24F4N2O3: 501.5 (MH+).

Sources & evidence

ORD record
ord-4c98cbdd32f04a599ef6d6f587fcb6fe
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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