Uses
Methyl 3-Hydroxyphenylacetate is a phenylacetic acid derivative and a CRTH2 and DP dual antagonist.
Synthesis
Step 1: 3-Hydroxyphenylacetic acid (15.2 g, 0.1 mol, 1.0 eq.) and concentrated sulfuric acid (392 mg, 4 mmol, 0.04 eq.) were dissolved in methanol (100 mL). The reaction mixture was stirred at room temperature for 1 h. The reaction was subsequently quenched with sodium hydroxide solution. The reaction mixture was extracted with ethyl acetate and the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate=5:1) to afford methyl 2-(3-hydroxyphenyl)acetate as a yellow oil (14.2 g, 86% yield).1H NMR (400 MHz, CDCl3) δ= 7.15-7.19 (m, 1H), 6.81 (d, 1H), 6.72-6.76 (m, 2H), 5.88 (m, 2H). 2H), 5.88 (s, 1H), 3.70 (s, 3H), 3.58 (s, 2H); LCMS m/z 167 [M + 1]+.
References
[1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 21, p. 5488 - 5492
[2] Patent: WO2004/63155, 2004, A1. Location in patent: Page 58
[3] Patent: WO2005/66136, 2005, A1. Location in patent: Page/Page column 51
[4] Patent: WO2005/19190, 2005, A2. Location in patent: Page/Page column 51
[5] Patent: WO2005/103050, 2005, A2. Location in patent: Page/Page column 168
