2-(5-Methyl-2-phenyl-4-oxazolyl)ethanol → HCID 66865094, compound
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][S:10][CH:11]([C:22]([O:24][CH2:25][C:26]([Cl:29])([Cl:28])[Cl:27])=[O:23])[CH2:12][C:13]2[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.[CH3:30][C:31]1[O:35][C:34]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[N:33][C:32]=1[CH2:42][CH2:43]O.C1(C2OC(C(F)(F)F)=C(COC(=O)C3C=CC(CC(SCCC4C=CC(F)=CC=4)C(OCC(Cl)(Cl)Cl)=O)=CC=3)N=2)C=CC=CC=1>>[CH3:30][C:31]1[O:35][C:34]([C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)=[N:33][C:32]=1[CH2:42][CH2:43][O:18][C:17](=[O:19])[C:16]1[CH:20]=[CH:21][C:13]([CH2:12][CH:11]([S:10][CH2:9][CH2:8][C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[C:22]([O:24][CH2:25][C:26]([Cl:29])([Cl:27])[Cl:28])=[O:23])=[CH:14][CH:15]=1Participants
Procedure
The title compound was prepared from 4-[2-[2-(4-fluoro-phenyl)-ethylsulfanyl]-2-(2,2,2-trichloro-ethoxycarbonyl)-ethyl]-benzoic acid (220 mg, 0.46 mmol) and 2-(5-methyl-2-phenyl-oxazol-4-yl)-ethanol (103 mg, 0.50 mmol) in the same manner as described for 4-[2-[2-(4-fluoro-phenyl)-ethylsulfanyl]-2-(2,2,2-trichloro-ethoxy-carbonyl)-ethyl]-benzoic acid 2-phenyl-5-trifluoromethyl-oxazol-4-ylmethylester. The crude product was purified by flash chromatography using n-heptane/EtOAc 7:3 as the eluent to afford the final product as an oil (280 mg, 83.5%). 1H NMR (400 MHz, CDCl3): δ 7.91-7.96 (m, 3H), 7.39-7.41 (m, 3H), 7.22-7.25 (m, 3H), 7.06-7.09 (m, 2H), 6.94 (t, 2H), 4.71 (m, 1H), 4.64 (m, 1H), 4.56 (t, 1H), 3.88-3.92 (m, 2H), 3.55 (m 1H), 3.29 (m, 1H), 2.69-2.04 (m, 6H), 2.32 (s, 3H). Mass Spectrum: M+H+ 666.14, M−H+ 664.39.
Workup
- customThe crude product was purified by flash chromatography
Sources & evidence
- ORD record
- ord-89a91d1ec2ec46d788c91e11b113b4d9
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09181181B2
Reaction notes
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