反应详情

N,N1 -Dicyclohexylcarbodiimide (10.3 g, 50 mmol) in methylene chloride (80 ml) was added to 2-acetylthio-3-methoxybenzoic acid (11.3 g, 50 mmol) and N-cyclopentylglycine t-butyl ester (10.0 g, 50 mmol) in methylene chloride (300 ml) at 0°-5° C. Overnight stirring was followed by filtration and washing of the filtrate with dilute hydrochloric acid, sodium bicarbonate solution and brine. Drying and concentration gave a gum which was dissolved in acetonitrile (65 ml), combined with sodium iodide (11.2 g, 75 mmol) and heated to 40°-50° C. Chlorotrimethylsilane (8.1 g, 75 mmol) was introduced and the mixture was heated for 30 minutes, then quenched with water. The organic phase was washed with water, aqueous sodium thiosulfate and brine then concentrated. Aqueous sodium bicarbonate was added to the residue and the resulting solution was washed with methylene chloride and ether, then acidified and extracted with ethyl acetate. The organic portion was dried and concentrated and the residue passed through a silica gel column to provide the amorphous product.

1. filtrationwas followed by filtration
2. washwashing of the filtrate with dilute hydrochloric acid, sodium bicarbonate solution and brine
3. customDrying
4. concentrationconcentration
5. customgave a gum which
6. temperatureheated to 40°-50° C
7. temperaturethe mixture was heated for 30 minutes
8. customquenched with water
9. washThe organic phase was washed with water, aqueous sodium thiosulfate and brine
10. concentrationthen concentrated
11. additionAqueous sodium bicarbonate was added to the residue
12. washthe resulting solution was washed with methylene chloride and ether
13. extractionextracted with ethyl acetate
14. customThe organic portion was dried
15. concentrationconcentrated
16. customto provide the amorphous product