(R)-Tetrahydro-3-furoic acid → HCID 45377295, compound

HRID 1630224Notes

Reaction equation

HRID 1630224 reaction equation
[O:1]1[CH2:5][CH2:4][CH:3]([C:6]([OH:8])=O)[CH2:2]1.[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:6]([CH:3]2[CH2:4][CH2:5][O:1][CH2:2]2)=[O:8])[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 4661317(R)-Tetrahydro-3-furoic acidHCID 67009148(2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide

Product 1

HCID 45377295HCID 45377295, compoundYield 28.3%

Procedure

Proceeding as in Example 1, but substituting tetrahydrofuran-3-carboxylic acid and (2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide, gave Compound 36, (2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)-1-(tetrahydrofuran-3-carbonyl)pyrrolidine-2-carboxamide (8.3 mg, 28.3%). 1H-NMR (400 MHz, DMSO-D6): σ 9.95 (s, 1H), 7.56 (m, 2H), 7.27 (m, 2H), 7.19 (m, 5H), 6.92 (m, 4H), 4.46 (m, 1H), 3.86 (m, 1H), 3.66 (m, 4H), 3.31 (m, 2H), 2.63 (m, 3H), 1.94 (m, 4H). MS (EI) for C29H29FN2O4: 489.5 (MH+).

Sources & evidence

ORD record
ord-3df8456df16345e19f1be63792820e3a
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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