Hydrochloric Acid → HCID 14428785, compound

109 mg of (22S)-1α,3β-diacetoxy-25-tetrahydropyranyloxy-cholest-5-en-23-yn-22-ol (IIIa1) was dissolved in a mixture of methanol and tetrahydrofuran, and after adding thereto 3 drops of 2N-hydrochloric acid, the mixture was stirred for 3 hours at room temperature. The reaction solution was diluted with ethyl acetate, and washed with saturated aqueous sodium hydrogen carbonate and water, successively. After drying with magnesium sulfate, the solvent was distilled away. The residue obtained was dissolved in 10 ml of ethyl acetate, and after adding thereto 10 mg of 10% Pd-C, the mixture was stirred for 4 hours at room temperature under an hydrogen stream atmosphere. The catalyst was filtered off, and the mixture was washed with ethyl acetate, and a combined solution of filtrate and washing was concentrated under reduced pressure. The residue was dissolved in 0.5 ml of pyridine, and after adding thereto 0.1 ml of acetic anhydride, the mixture was stirred overnight at room temperature. After adding water to the reaction solution, the mixture was extracted with ethyl acetate. The extract organic layer was washed with 2N-hydrochloric acid, saturated aqueous sodium hydrogen carbonate, and water, successively, and dried over magnesium sulfate. The solvent was distilled away, and the residue was subjected to column chromatography (n-hexane-ethyl acetate=4:1) for purification to give 71.6 mg of (22R)-1α,3β,22-triacetoxycholest-5-en-25-ol (IVa1). (IVa1): Oily material

1. additionafter adding
2. washwashed with saturated aqueous sodium hydrogen carbonate and water
3. dry with materialAfter drying with magnesium sulfate
4. distillationthe solvent was distilled away
5. customThe residue obtained
6. additionafter adding
7. filtrationThe catalyst was filtered off
8. washthe mixture was washed with ethyl acetate
9. washa combined solution of filtrate and washing
10. concentrationwas concentrated under reduced pressure
11. dissolutionThe residue was dissolved in 0.5 ml of pyridine
12. additionafter adding
13. additionAfter adding water to the reaction solution
14. extractionthe mixture was extracted with ethyl acetate
15. washThe extract organic layer was washed with 2N-hydrochloric acid, saturated aqueous sodium hydrogen carbonate, and water
16. dry with materialsuccessively, and dried over magnesium sulfate
17. distillationThe solvent was distilled away
18. customthe residue was subjected to column chromatography (n-hexane-ethyl acetate=4:1) for purification

ORD record

ord-27bfa7015a1d441ba538deaba025808b

Source dataset

uspto-grants-1990_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04897387