Triacetoxyperiodinane → HCID 178437011, compound

Participants

Reaction Steps

N-[1-(tert-Butyl-diphenyl-silanyloxymethyl)-2-hydroxy-1-methyl-ethyl]-2-(3-ethynyl-quinolin-6-yloxy)-2-methylsulfanyl-acetamide (1.90 g) from Stage 2 above in dichloromethane (55 ml) was treated with Dess-Martin periodinane (1.615 g). The reaction mixture was stirred at R.T. for 1 h 30 and then, quenched with sat. aqueous NaHCO3 and sat. aqueous sodium thiosulphate. The reaction mixture was vigorously stirred at rt. for 50 minutes after which time the two phases were separated. The organic layer was washed thrice with sat. aqueous. NaHCO3. After separation, the organic phase was dried over sodium sulphate, filtered and evaporated to yield 1.694 g of N-[1-(tert-Butyl-diphenyl-silanyloxymethyl)-1-methyl-2-oxo-ethyl]-2-(3-ethynyl-quinolin-6-yloxy)-2-methylsulfanyl-acetamide as a crude product along with minor impurities. The crude mixture was used in the next step without any further purification.

Provenance & Evidence