Triethylamine → HCID 123486832, compound

Participants

Reaction Steps

To Compound (5) (450 mg, 0.56 mmole) in dry methanol (7.5 mL) was added under stirring 1,3-propanedithiol (0.284 mL, 2.82 mmole) followed by triethylamine (0.394 mL, 2.82 mmole). The mixture was stirred at room temperature for 5 days. The mixture was diluted with methanol (7 mL) and ethyl trifluoroacetate (0.675 mL, 5.6 mole) and triethylamine (0.237 mL, 1.7 mole) was added. Stirring at room temperature was continued for 24 hours. The resulting suspension was diluted with dichloromethane (5 mL) and the solvent was removed under reduced pressure. Column chromatography on silica gel with ethyl acetate/hexane mixtures gave 5'-O-(4,4'-dimethoxytrityl)-3'-O-[(dimethyl-1,1-dimethylethyl)silyl]-4'-(7-trifluoroacetamido-1-hepten-1-yl)-thymidine (6) (371 mg, 76%), m.p. 75°-76° C.

Provenance & Evidence