Chlorotrimethylsilane → 2-((S)-2-{(R)-2-amino-2-[4-((S)-2,3-bis-trimethylsilanyloxy-propoxy)-phenyl]-acetylamino}-3-phenyl-propionylamino)-thiazole-4-carboxylic acid methyl ester

Participants

Reaction Steps

Chloro-trimethyl-silane (0.086 ml, 0.68 mmol) was added to 2-((S)-2-{(R)-2-amino-2-[4-((R)-2,3-dihydroxy-propoxy)-phenyl]-acetylamino}-3-phenyl-propionylamino)-thiazole-4-carboxylic acid methyl ester (120 mg, 0.23 mmol) in tetrahydrofuran (5 mL) containing triethylamine (0.10 ml, 0.73 mmol) at room temperature and stirred for 3 hours. The mixture was diluted with water and extracted with ethyl acetate. The organic extracts were washed with water, brine and dried over magnesium sulfate. Removal of solvents gave 2-((S)-2-{(R)-2-amino-2-[4-((S)-2,3-bis-trimethylsilanyloxy-propoxy)-phenyl]-acetylamino}-3-phenyl-propionylamino)-thiazole-4-carboxylic acid methyl ester as an oil (100 mg, 66%).

Provenance & Evidence