Triethylsilane → (2S)-3-(4-benzyloxy-2-ethyl-phenyl)-2-ethoxy-propionic acid methyl ester

Triethylsilane (3.2 ml, 20 mmol) was added to a vigorously stirred, ice-cooled solution of (2S,3R)-3-(4-benzyloxy-2-ethyl-phenyl)-2-ethoxy-3-hydroxy-propionic acid methyl ester (720 mg, 2 mmol) in trifluoroacetic acid (10 ml) under an argon atmosphere. The mixture was stirred at 0° C. for 30 min and for additional 2 h at ambient temperature. The solution was poured onto crashed ice and extracted with ethyl acetate. The organic layer was washed two times with water and neutralized with saturated aqueous sodium bicarbonate solution. The ethyl acetate layer was washed with brine and dried over sodium sulfate. The solvent was removed under reduced pressure to give a colorless oil which was purified by column chromatography (silica gel, cyclohexane/AcOEt) to yield 390 mg (1.1 mmol, 57%) of the title compound as colorless liquid.

1. stirringThe mixture was stirred at 0° C. for 30 min and for additional 2 h at ambient temperature
2. additionThe solution was poured
3. extractionextracted with ethyl acetate
4. washThe organic layer was washed two times with water
5. washThe ethyl acetate layer was washed with brine
6. dry with materialdried over sodium sulfate
7. customThe solvent was removed under reduced pressure
8. customto give a colorless oil which
9. customwas purified by column chromatography (silica gel, cyclohexane/AcOEt)

ORD 기록

ord-6d9eebbc5c104d31842211831e70e7c1

출처 데이터셋

uspto-grants-2006_09

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07109225B2