Trifluoroacetic acid → HCID 86584846, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 281 mg (2.0 mmol, 4 eq.) potassium carbonate in 2 ml DMSO were added 300 mg (0.51 mmol) (2S,4R)-2-azidomethyl-1-(naphthalene-2-sulfonyl)-4-tritylsulfanyl-pyrrolidine and 72 μl (0.7 mmol, 1.38 eq) acetyl acetone. The reaction mixture was stirred at 40° C. for 3 d, diluted with water and extracted with Et2O, the layers were separated and the inorganic one was extracted with EtOAc, the combined organic layers were washed with brine, dried over Na2SO4 and evaporated. The residue was purified by column chromatography on silica gel with EtOAc/hexane 1:1 yielding 249 mg (73%) (2S,4R)-1-{5-methyl-1-[1-(naphthalene-2-sulfonyl)-4-tritylsulfanyl-pyrrolidin-2-ylmethyl]-1H-[1,2,3]triazol-4-yl}-ethanone as white foam, MS: 673 (MH+). 150 mg (0.2 mmol) (2S,4R)-1-{5-methyl-1-[1-(naphthalene-2-sulfonyl)-4-tritylsulfanyl-pyrrolidin-2-ylmethyl]-1H-[1,2,3]triazol-4-yl}-ethanone were dissolved in 6.5 ml acetonitrile and 3 ml TFA and were treated with 0.5 ml triethylsilane at 40° C. for 4 h. The reaction mixture was added to a aqueous saturated NaHCO3 solution carefully, extracted, and the organic layer was washed with water and brine, dried over Na2SO4 and evaporated. Purification by column chromatography on silica gel with EtOAc/hexane 1:1 gave 63 mg (66%) (2S,4R)-1-[1-[4-mercapto-1-(naphthalene-2-sulfonyl)-pyrrolidin-2-ylmethyl]-5-methyl-1H-[1,2,3]triazol-4-yl]-ethanone as white solid, mp 145° C., MS: 431 (MH+).

Provenance & Evidence