Lithium Hydroxide → HCID 21051842, compound

Temperature

25 °C

A solution of 2-(4-methylsulfanyl-phenyl)-3-(tetrahydro-furan-2(R)-yl)-propionic acid methyl ester (0.693 g, 2.47 mmol) in methanol (10 mL) was treated with a 0.8M aqueous lithium hydroxide solution (4.01 mL, 4.94 mmol). The reaction mixture was stirred at 25° C. for 16 h and then was concentrated in vacuo to remove methanol. The remaining aqueous layer was acidified to pH=2 with a 10% aqueous hydrochloric acid solution and then was extracted with ethyl acetate (2×10 mL). The combined organic layers were washed with a saturated aqueous sodium chloride solution (1×10 mL), dried over sodium sulfate, filtered, and concentrated in vacuo to afford pure 2-(4-methylsulfanyl-phenyl)-3-(tetrahydro-furan-2(R)-yl)-propionic acid (0.653 g, 99%) as a light yellow oil that crystallized upon standing: mp 105–107° C.; [α]23589=−14.93° (c=0.75, chloroform); EI-HRMS m/e calcd for C14H18O3S (M+) 266.0976, found 266.0976.

1. concentrationwas concentrated in vacuo
2. customto remove methanol
3. extractionwas extracted with ethyl acetate (2×10 mL)
4. washThe combined organic layers were washed with a saturated aqueous sodium chloride solution (1×10 mL)
5. dry with materialdried over sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated in vacuo

ORD record

ord-2f12785f5fa844ae92c171dd27b32495

Source dataset

uspto-grants-2006_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07105671B2