Sodium Hydroxide → HCID 69672744, Verbindung

To a solution of Methyl (2S)-tert-butoxy[4-(4-chlorophenyl)-2-methyl-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridin-3-yl]acetate (60 mg, 131 μmol) in tetrahydrofuran (2 mL) and methylated spirit (2 mL) was added an aqueous sodium hydroxide solution (1 M, 790 μL, 790 μmol). The resulting solution was stirred at 60° C. for 3 hours. The volatile solvents were removed in vacuo and the residue diluted with water (10 mL). Dichloromethane (20 mL) was added to the mixture, which was then acidified to pH 5 by the addition of 2 M aqueous hydrochloric acid. The organic layer was separated and washed with water (10 mL) and brine (10 mL), dried over MgSO4 and concentrated in vacuo. The residue was recrystallised from 2-propanol and the resulting solid collected by filtration to give the title compound as a white solid, 11.2 mg, in a 19% yield.

1. customThe volatile solvents were removed in vacuo
2. additionthe residue diluted with water (10 mL)
3. additionDichloromethane (20 mL) was added to the mixture, which
4. additionwas then acidified to pH 5 by the addition of 2 M aqueous hydrochloric acid
5. customThe organic layer was separated
6. washwashed with water (10 mL) and brine (10 mL)
7. dry with materialdried over MgSO4
8. concentrationconcentrated in vacuo
9. customThe residue was recrystallised from 2-propanol
10. filtrationthe resulting solid collected by filtration

ORD-Eintrag

ord-3e67e602e19e40059d4308b0f83a905b

Quelldatensatz

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08809363B2