Lithium hydroxide, monohydrate → 8-(5-Methyl-2-phenyl-oxazol-4-yl)-2-thiophen-2-yl-oct-4-ynoic acid
Reaction equation
C([O:3][C:4](=[O:29])[CH:5]([C:24]1[S:25][CH:26]=[CH:27][CH:28]=1)[CH2:6][C:7]#[C:8][CH2:9][CH2:10][CH2:11][C:12]1[N:13]=[C:14]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[O:15][C:16]=1[CH3:17])C.O[Li].O>>[CH3:17][C:16]1[O:15][C:14]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[N:13][C:12]=1[CH2:11][CH2:10][CH2:9][C:8]#[C:7][CH2:6][CH:5]([C:24]1[S:25][CH:26]=[CH:27][CH:28]=1)[C:4]([OH:29])=[O:3]Participants
3
Procedure
The ester 1-12 was then hydrolyzed in a manner similar to the preparation of 1-11 with LiOH.H2O to provide 90 mg of acid 1-13 (47% yield). NMR CDCl3 (δ): 7.97 (2H, m); 7.43 (3H, m); 7.21 (1H, d, J=5.1 Hz); 7.06 (1H, d, J=3.1 Hz); 6.96 (1H, m); 4.21 (1H, dd, J=5.3, 10.7 Hz); 2.89 (2H, m); 2.62 (2H, m); 2.34 (3H, s); 2.23 (2H, m); 1.82 (2H, m). M+1=363.2. Biological Data: EC50=303 nM in AD3T3-L1 reporter assay. Maximal response of 97% rosiglitazone.
Sources & evidence
- ORD record
- ord-fdc19262122c4ba6ac969ff910005c0a
- Source dataset
- uspto-grants-2004_02
- Patent number
- US06696474B2
Reaction notes
Loading…