Lithium hydroxide, monohydrate → 3-[Isopropyl-(3-methyl-cyclopent-3-enecarbonyl)-amino]-5-phenyl-thiophene-2-carboxylic acid
Reaction equation
C[O:2][C:3]([C:5]1[S:6][C:7]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:8][C:9]=1[N:10]([CH:19]([CH3:21])[CH3:20])[C:11]([CH:13]1[CH2:17][CH:16]=[C:15]([CH3:18])[CH2:14]1)=[O:12])=[O:4].O[Li].O>>[CH:19]([N:10]([C:11]([CH:13]1[CH2:17][CH:16]=[C:15]([CH3:18])[CH2:14]1)=[O:12])[C:9]1[CH:8]=[C:7]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[S:6][C:5]=1[C:3]([OH:4])=[O:2])([CH3:21])[CH3:20]Participants
3
Procedure
Saponification of 3-[Isopropyl-(3-methyl-cyclopent-3-enecarbonyl)-amino]-5-phenyl-thiophene-2-carboxylic acid methyl ester (50 mg, 0.13 mmol) using LiOH.H2O (22 mg) as previously described furnished the 3-[Isopropyl-(3-methyl-cyclopent-3-enecarbonyl)-amino]-5-phenyl-thiophene-2-carboxylic acid (30 mg, 62.5% yield) as a solid. 1H NMR (CD3OD, 400 MHz 1:1 mixture of rotamers) 7.73-7.70 (m, 4H), 7.47-7.35 (m, 6H), 7.29 (s, 1H), 7.27 (s, 1H), 5.16 (s, 1H), 5.08 (s, 1H), 4.9-4.8 (m, 2H), 3.15-3.05 (m, 2H), 2.76-2.65 (m, 2H), 2.42-2.12 (m, 6H), 1.65 (s, 3H), 1.61 (s, 3H), 1.25 (d, J=6.6 Hz, 3H), 1.24 (d, J=6.6 Hz, 3H), 1.03 (d, J=6.9 Hz, 6H).
Sources & evidence
- ORD record
- ord-82095ca89bb84ad68922007f37a9e44b
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07985769B2
Reaction notes
Loading…