Hydrochloric Acid → (S)-3-(1-methoxypropan-2-yloxy)-5-(4-(methylsulfonyl)phenoxy)benzoic acid

3-[(1S)-2-Methoxy-1-methylethoxy]-5-[4-(methylsulfonyl)phenoxy]benzonitrile (0.1 g, 0.27 mmol) was dissolved in ethanol (1.0 ml) and charged to a 5 ml round bottomed flask equipped with condenser and magnetic stirrer. Water (0.2 ml, 11.1 mmol) was added, followed by sodium hydroxide (18.9M in water, 0.2 ml, 3.78 mmol). The reaction mixture was heated to reflux for 18 hours. The reaction mixture was cooled to ambient temperature, and the solvent was evaporated in vacuo. The residue was partitioned between water (10 ml) and MTBE (10 ml) and the layers were separated. The aqueous phase was acidified to pH1 with 2M HCl (2.5 ml, 5 mmol) and MTBE (10 ml) was added to extract the product. The MTBE extract was dried over MgSO4, and then evaporated in vacuo to afford a pale yellow oil (0.1 g, 100% yield).

1. additioncharged to a 5 ml round bottomed flask
2. customequipped with condenser and magnetic stirrer
3. temperatureThe reaction mixture was heated
4. temperatureto reflux for 18 hours
5. customthe solvent was evaporated in vacuo
6. customThe residue was partitioned between water (10 ml) and MTBE (10 ml)
7. customthe layers were separated
8. additionwas added
9. extractionto extract the product
10. extractionThe MTBE extract
11. dry with materialwas dried over MgSO4
12. customevaporated in vacuo

ORD record

ord-7888ffb3cd1e470a89948ffc27a7f95a

Source dataset

uspto-grants-2010_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07700640B2