5-Methyl-2-phenyl-4-oxazoleacetic acid → HCID 118491834, compound

HRID 709460Notes

Reaction equation

HRID 709460 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.[CH3:29][C:30]1[O:34][C:33]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[N:32][C:31]=1[CH2:41][C:42](O)=[O:43].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>>[Cl:28][C:2]([Cl:27])([Cl:1])[CH2:3][O:4][C:5](=[O:26])[CH:6]([S:16][CH2:17][CH2:18][C:19]1[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=1)[CH2:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:14][O:15][C:42](=[O:43])[CH2:41][C:31]2[N:32]=[C:33]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[O:34][C:30]=2[CH3:29])=[CH:12][CH:13]=1

Participants

4

Reactant 3

HCID 27751395-Methyl-2-phenyl-4-oxazoleacetic acidHCID 44185046HCID 44185046, compoundHCID 86650303HCID 86650303, compound

Product 1

HCID 118491834HCID 118491834, compound

Procedure

The title compound was prepared from 2-[2-(4-fluoro-phenyl)-ethylsulfanyl]-3-(4-hydroxymethyl-phenyl)-propionic acid 2,2,2-trichloroethyl ester (512 mg, 1.1 mmol) and 2-(5-methyl-2-phenyl-oxazol-4-yl)-acetic acid (261 mg, 1.2 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-ylmethyl ester. The product was obtained without further purification as an oil (751 mg, 94.1%). 1H NMR (500 MHz, CDCl3): δ 8.06 (d, 2H), 7.44 (m, 3H), 7.29 (m, 2H), 7.20 (d, 2H), 7.10-7.13 (m, 2H), 6.98 (t, 2H), 5.16 (s, 2H), 4.73 (q, 2H), 3.58 (dd, 1H), 3.22 (dd, 1H), 2.84-3.00 (m, 5H). Mass Spectrum: M+H+666.00.

Sources & evidence

ORD record
ord-02a26c2a106e4c9598e1d22b32743584
Source dataset
uspto-grants-2015_11
Patent number
US09181181B2

Reaction notes

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