2-Phenyl-5-(trifluoromethyl)-oxazole-4-carboxylic acid → 2-Phenyl-5-trifluoromethyl-oxazole-4-carboxylic acid 4-[2-[2-(4-fluoro-phenyl)ethylsulfanyl]-2-(2,2,2-trichloro-ethoxycarbonyl)-ethyl]-benzyl ester

HRID 709458Notes

Reaction equation

HRID 709458 reaction equation
[Cl:1][C:2]([Cl:28])([Cl:27])[CH2:3][O:4][C:5](=[O:26])[CH:6]([S:16][CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][OH:15])=[CH:10][CH:9]=1.[C:29]1([C:35]2[O:36][C:37]([C:43]([F:46])([F:45])[F:44])=[C:38]([C:40](O)=[O:41])[N:39]=2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.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>>[F:25][C:22]1[CH:21]=[CH:20][C:19]([CH2:18][CH2:17][S:16][CH:6]([C:5]([O:4][CH2:3][C:2]([Cl:27])([Cl:1])[Cl:28])=[O:26])[CH2:7][C:8]2[CH:9]=[CH:10][C:11]([CH2:14][O:15][C:40]([C:38]3[N:39]=[C:35]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[O:36][C:37]=3[C:43]([F:45])([F:46])[F:44])=[O:41])=[CH:12][CH:13]=2)=[CH:24][CH:23]=1

Participants

4

Reactant 3

HCID 27764382-Phenyl-5-(trifluoromethyl)-oxazole-4-carboxylic acidHCID 441850462-[2-(4-Fluoro-phenyl)-ethylsulfanyl]-3-(4-hydroxymethyl-phenyl)-propionic acid 2,2,2-trichloro-ethyl esterHCID 86650303HCID 86650303, compound

Product 1

HCID 866503042-Phenyl-5-trifluoromethyl-oxazole-4-carboxylic acid 4-[2-[2-(4-fluoro-phenyl)ethylsulfanyl]-2-(2,2,2-trichloro-ethoxycarbonyl)-ethyl]-benzyl ester

Procedure

The title compound was prepared from 2-[2-(4-fluoro-phenyl)-ethylsulfanyl]-3-(4-hydroxymethyl-phenyl)-propionic acid 2,2,2 trichloro-ethyl ester (675 mg, 1.45 mmol) and 2-phenyl-5-trifluoromethyl-oxazole-4-carboxylic acid (410 mg, 1.59 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 obtained as an oil which was carried on to the next step without further purification (892 mg, 79.4%). 1H NMR (500 MHz, CDCl3): δ 8.15 (d, 2H), 7.57 (d, 1H), 7.52 (t, 2H), 7.41 (d, 2H), 7.12 (t, 2H), 6.97 (t, 2H), 5.42 (s, 2H), 4.72 (q, 2H), 3.59 (dd, 1H), 3.25 (dd, 1H), 2.78-3.05 (m, 5H). Mass Spectrum: M+H+ 705.89.

Sources & evidence

ORD record
ord-7944a7da30714d17b86e841d8054de0e
Source dataset
uspto-grants-2015_11
Patent number
US09181181B2

Reaction notes

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