Hydroxylamine → 6-(4'-Chloro-biphenyl-4-ylsulfanyl)-hexanoic acid

Temperatur

0 °C

To a solution of 6-(4′-chloro-biphenyl-4-ylsulfanyl)-hexanoic acid methyl ester (1.0 g, 2.9 mmol) in distilled THF (20 mL) containing 50% aqueous hydroxylamine (1.9 mL, 28.8 mmol) was added at 0° C. a solution of potassium hydroxide in methanol (5.0 mL, 1M, 5.0 mmol) in a dropwise manner. After stirring at 0° C. for 1 h, distilled water (20 mL) was added and the mixture was made neutral by dropwise addition of concentrated hydrochloric acid (10 M) at 0° C. The aqueous solution was extracted with ethyl acetate (2×40 mL) and the combined extracts were washed with brine (80 mL), dried over anhydrous MgSO4, filtered and evaporated to dryness. The residue was recrystallised from acetone to give the title compound (923 mg, 91%) as a white powder, mp 156-157° C.

1. distillationdistilled water (20 mL)
2. additionwas added
3. additionthe mixture was made neutral by dropwise addition of concentrated hydrochloric acid (10 M) at 0° C
4. extractionThe aqueous solution was extracted with ethyl acetate (2×40 mL)
5. washthe combined extracts were washed with brine (80 mL)
6. dry with materialdried over anhydrous MgSO4
7. filtrationfiltered
8. customevaporated to dryness
9. customThe residue was recrystallised from acetone

ORD-Eintrag

ord-5dc331e3b0334694a85be06bbff59b54

Quelldatensatz

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07683185B2