Tetrahydrofuran → (+/-)-[4-Chloro-2-(4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridin-4-yl)-phenoxyl]-acetic acid isopropyl ester

To a solution of (±)-[4-chloro-2-(4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridin-4-yl)-phenoxy]-acetic acid ethyl ester hydrochloride (1.70 g, 4.37 mmol, 1 eq.) in THF (50 mL) and EtOH (25 mL), 1M aq. NaOH (50 mL) was added. The pale yellow solution was stirred at r.t. for 18 hours, then concentrated in vacuo. The resulting aq. layer was carefully acidified with 2N aq. HCl. The mixture was extracted with DCM (3×100 mL). The comb. org. phases were dried over MgSO4 and concentrated in vacuo. The residue was dissolved in 5-6N HCl in 2-propanol (150 mL). The reaction mixture was stirred at r.t. for 18 hours. The mixture was concentrated in vacuo. The reaction was diluted with sat. aq. NaHCO3 (250 mL). The mixture was extracted with DCM (3×200 mL). The comb. org. phases were dried over MgSO4 and concentrated in vacuo to give the title compound as a yellow solid. The product was used without further purification.

1. concentrationconcentrated in vacuo
2. extractionThe mixture was extracted with DCM (3×100 mL)
3. dry with materialphases were dried over MgSO4
4. concentrationconcentrated in vacuo
5. dissolutionThe residue was dissolved in 5-6N HCl in 2-propanol (150 mL)
6. stirringThe reaction mixture was stirred at r.t. for 18 hours
7. concentrationThe mixture was concentrated in vacuo
8. additionThe reaction was diluted with sat. aq. NaHCO3 (250 mL)
9. extractionThe mixture was extracted with DCM (3×200 mL)
10. dry with materialphases were dried over MgSO4
11. concentrationconcentrated in vacuo

ORD record

ord-b13891fb13144b6b91f3c680bbf52fe9

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09169270B2