(2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide → HCID 67009839, compound

HRID 1630222Notes

Reaction equation

HRID 1630222 reaction equation
Cl.[CH2:2]([O:6][CH2:7][C:8]([OH:10])=O)[CH2:3][CH2:4][CH3:5].[CH2:11]([C@H:18]1[CH2:22][NH:21][C@H:20]([C:23]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([O:32][C:33]3[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=3)=[CH:28][CH:27]=2)=[O:24])[CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[CH2:11]([C@H:18]1[CH2:22][N:21]([C:8](=[O:10])[CH2:7][O:6][CH2:2][CH2:3][CH2:4][CH3:5])[C@H:20]([C:23]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([O:32][C:33]3[CH:34]=[CH:35][C:36]([F:39])=[CH:37][CH:38]=3)=[CH:28][CH:27]=2)=[O:24])[CH2:19]1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

3

Reactant 2

HCID 67009148(2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamideHCID 86659489HCID 86659489, compound

Product 1

HCID 67009839HCID 67009839, compoundYield 30.1%

Procedure

Proceeding as in Example 1, but substituting 2-butoxyacetic acid hydrochloride and (2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide, gave Compound 38, (2S,4R)-4-benzyl-1-(2-butoxyacetyl)-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide (9.1 mg, 30.1%). 1H-NMR (400 MHz, DMSO-D6): σ 9.95 (s, 1H), 7.56 (m, 2H), 7.27 (m, 2H), 7.19 (m, 5H), 6.96 (m, 4H), 4.47 (t, 1H), 4.03 (t, 1H), 3.60 (m, 1H), 3.42 (m, 2H), 3.29 (m, 2H), 2.65 (m, 3H), 1.89 (m, 2H), 1.35 (m, 4H), 0.85 (t, 3H). MS (EI) for C30H33FN2O4: 505.4 (MH+).

Sources & evidence

ORD record
ord-dc1f801f20544070a270334d3c5c16b1
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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