(2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide → HCID 67010440, compound

HRID 1630198Notes

Reaction equation

HRID 1630198 reaction equation
Cl.[CH3:2][O:3][CH2:4][C:5]([OH:7])=O.[CH2:8]([C@H:15]1[CH2:19][NH:18][C@H:17]([C:20]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][C:30]3[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=3)=[CH:25][CH:24]=2)=[O:21])[CH2:16]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>>[CH2:8]([C@H:15]1[CH2:19][N:18]([C:5](=[O:7])[CH2:4][O:3][CH3:2])[C@H:17]([C:20]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][C:30]3[CH:31]=[CH:32][C:33]([F:36])=[CH:34][CH:35]=3)=[CH:25][CH:24]=2)=[O:21])[CH2:16]1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

3

Reactant 2

HCID 67009148(2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamideHCID 86659477HCID 86659477, compound

Product 1

HCID 67010440HCID 67010440, compoundYield 43.2%

Procedure

Proceeding as in Example 1, but substituting 2-methoxyacetic acid hydrochloride and (2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide, gave Compound 122, (2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)-1-(2-methoxyacetyl)pyrrolidine-2-carboxamide (12 mg, 43.2%); Major isomer: 1H-NMR (400 MHz, DMSO-D6): σ 9.97 (s, 1H), 7.56-7.59 (m, 2H), 7.28-7.32 (m, 2H), 7.17-7.23 (m, 5H), 6.94-7.02 (m, 4H), 4.50 (m, 1H), 4.04 (m, 1H), 3.60 (m, 1H), 3.28 (s. 3H), 3.18 (m, 2H), 2.65 (m, 3H), 1.90 (m, 2H). MS (EI) for C27H27FN2O4. found 463.5 (MH+).

Sources & evidence

ORD record
ord-cb18a0e2d94849fe9345067a0b62cea2
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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