Chlorotrimethylsilane → HCID 59263942, compound

Participants

Reaction Steps

To an ice cooled suspension of benzyl 2-(4-hydroxy-2-oxo-2,3-dihydrobenzo[d]thiazol-7-yl)ethyl(2-(tetrahydro-2H-pyran-4-ylamino)ethyl)carbamate (2.5 g), as prepared as in Example 23 step i), in dichloromethane (40 mL) was added triethylamine (2.95 mL) followed by chlorotrimethylsilane (2.69 mL). The reaction was allowed to stir for 30 min before a solution of the acid chloride of step i) (2.198 g) in dichloromethane (20 mL) was added. The reaction was stirred for 2 h before the mixture was diluted with dichloromethane (200 mL), washed with water (150 mL) and saturated sodium hydrogen carbonate (150 mL), and the organic layer was dried over sodium sulphate, filtered and evaporated to afford crude product. This was purified by flash silica chromatography eluting with ethyl acetate. Pure fractions were evaporated to dryness to afford the sub-title product (3.10 g) as a off-white foam.

Provenance & Evidence