(2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide → HCID 67010455, compound

HRID 1630210Notes

Reaction equation

HRID 1630210 reaction equation
Cl.[C:2]([N:5]1[CH2:9][CH2:8][CH2:7][C@H:6]1[C:10](O)=[O:11])(=[O:4])[CH3:3].[CH2:13]([C@H:20]1[CH2:24][NH:23][C@H:22]([C:25]([NH:27][C:28]2[CH:33]=[CH:32][C:31]([O:34][C:35]3[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH:36]=3)=[CH:30][CH:29]=2)=[O:26])[CH2:21]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[C:2]([N:5]1[CH2:9][CH2:8][CH2:7][C@H:6]1[C:10]([N:23]1[CH2:24][C@H:20]([CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:21][C@H:22]1[C:25]([NH:27][C:28]1[CH:33]=[CH:32][C:31]([O:34][C:35]2[CH:36]=[CH:37][C:38]([F:41])=[CH:39][CH:40]=2)=[CH:30][CH:29]=1)=[O:26])=[O:11])(=[O:4])[CH3:3]

Participants

3

Reactant 2

HCID 67009148(2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamideHCID 67010425HCID 67010425, compound

Product 1

HCID 67010455HCID 67010455, compoundYield 36.2%

Procedure

Proceeding as in Example 1, but substituting (S)-1-acetylpyrrolidine-2-carboxylic acid hydrochloride and (2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide, gave Compound 93, (2S,4R)-1-((S)-1-acetylpyrrolidine-2-carbonyl)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide (11.5 mg, 36.2%). Major isomer: 1H-NMR (400 MHz, DMSO-D6): σ 9.96 (s, 1H), 7.54 (m, 2H), 7.29-7.24 (m, 4H), 7.20-7.14 (m, 5H), 6.93 (m, 2H), 4.46 (m, 2H), 3.47-3.37 (m, 4H), 2.66 (m, 2H), 1.95-1.83 (m, 8H), 1.76-1.69 (m, 2H). MS (EI) for C31H32FN3O4. found 530.6 (MH+).

Sources & evidence

ORD record
ord-f1e2e5669b4e4602964f3650576d4b44
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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