(2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide → HCID 45377296, compound

HRID 1630220Notes

Reaction equation

HRID 1630220 reaction equation
Cl.[OH:2][C@H:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:4]([OH:6])=O.[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>>[CH2:13]([C@H:20]1[CH2:24][N:23]([C:4](=[O:6])[C@H:3]([OH:2])[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C@H:22]([C:25]([NH:27][C:28]2[CH:33]=[CH:32][C:31]([O:34][C:35]3[CH:36]=[CH:37][C:38]([F:41])=[CH:39][CH:40]=3)=[CH:30][CH:29]=2)=[O:26])[CH2:21]1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

3

Reactant 2

HCID 67009148(2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamideHCID 67010210HCID 67010210, compound

Product 1

HCID 45377296HCID 45377296, compoundYield 26.7%

Procedure

Proceeding as in Example 1, but substituting (R)-2-hydroxy-2-phenylacetic acid hydrochloride and (2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide, gave Compound 40, (2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)-1-((R)-2-hydroxy-2-phenylacetyl)pyrrolidine-2-carboxamide (8.4 mg, 26.7%). 1H-NMR (400 MHz, DMSO-D6): σ 10.03 (s, 1H), 7.56 (d, 2H), 7.27 (m, 11H), 6.97 (m, 5H), 5.20 (s, 1H), 4.44 (t, 1H), 2.86 (t, 2H), 2.71 (s, 1H), 2.45 (d, 2H), 1.80 (m, 2H). MS (EI) for C32H29FN2O4: 525.4 (MH+).

Sources & evidence

ORD record
ord-3ea181ab4b6c4dc294b49f629e01d9f7
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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