Potassium Iodide → [Rac]-2-ethoxy-3-[2-methyl-4-(5-methyl-2-thiophen-2-yl-oxazol-4-ylmethoxy)-phenyl]-propionic acid ethyl ester
Reaction equation
[CH2:1]([O:3][C:4](=[O:18])[CH:5]([O:15][CH2:16][CH3:17])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][C:8]=1[CH3:14])[CH3:2].Cl[CH2:20][C:21]1[N:22]=[C:23]([C:27]2[S:28][CH:29]=[CH:30][CH:31]=2)[O:24][C:25]=1[CH3:26].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>>[CH2:1]([O:3][C:4](=[O:18])[CH:5]([O:15][CH2:16][CH3:17])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:20][C:21]2[N:22]=[C:23]([C:27]3[S:28][CH:29]=[CH:30][CH:31]=3)[O:24][C:25]=2[CH3:26])=[CH:9][C:8]=1[CH3:14])[CH3:2]Participants
Reactant 4
Product 1
Procedure
In analogy to the procedure described in example 120 f], [rac]-2-ethoxy-3-(4-hydroxy-2-methyl-phenyl)-propionic acid ethyl ester (example 129 c]) was reacted with 4-chloromethyl-5-methyl-2-thiophen-2-yl-oxazole in the presence of potassium carbonate and potassium iodide to yield [rac]-2-ethoxy-3-[2-methyl-4-(5-methyl-2-thiophen-2-yl-oxazol-4-ylmethoxy)-phenyl]-propionic acid ethyl ester, which was further saponified in analogy to the procedure described in example 120 f] to yield [rac]-2-ethoxy-3-[2-methyl-4-(5-methyl-2-thiophen-2-yl-oxazol-4-ylmethoxy)-phenyl]-propionic acid as light yellow solid. MS: 400.3 (M−H)−, 354.1, 281.2. NMR: (CDCl3, 1H, 300 MHz, δ, TMS) 1.13 (t, J=7.2, 3H), 2.34 (s, 3H), 2.41 (s, 3H), 2.93 (d×d, J=15.2, J=8.8, 1H), 3.12 (d×d, J=15.2, J=4, 1H), 3.30-3.38 (m, 1H), 3.49-3.57 (m, 1H), 4.01 (d×d, J=8, J=4.8, 1H), 4.94 (s, 2H), 6.78 (d×d, J=8, J=1.6, 1H), 6.82 (d, J=1.6, 1H), 7.08-7.14 (m, 2H), 7.40 (d×d, J=4.8, J=0.8, 1H), 7.64 (d×d, J=4.0, J=0.8, 1H).
Sources & evidence
- ORD record
- ord-d4020956ccd7483684c7226fee30c15c
- Source dataset
- uspto-grants-2003_11
- Patent number
- US06642389B2
Reaction notes
Loading…