Triethylamine → HCID 86690947, compound

Participants

Reaction Conditions

Reaction Steps

230 mg (0.39 mmol) of the compound from Example 134 were dissolved in 5 ml of THF, the solution was cooled to 0° C. and 55 μl (0.39 mmol) of triethylamine and also 56 μl (0.43 mmol) of isobutyl chloroformate were added. The mixture was stirred at 0° C. for 1 h. The suspension was then filtered through a Seitz frit into a flask cooled to 0° C., and the residue was rinsed with about 2 ml of THF. With vigorous stirring, this solution was added to a solution, cooled to 0° C., of 44 mg (1.18 mmol) of sodium borohydride in 0.6 ml of water. After 1 h, 5 ml of saturated aqueous sodium bicarbonate solution were added, and the mixture was warmed to RT. The mixture was extracted with 15 ml of ethyl acetate. The organic phase was washed successively with in each case 5 ml of saturated sodium bicarbonate solution and saturated sodium chloride solution. After drying over sodium sulfate, the mixture was filtered and concentrated under reduced pressure. The crude product was purified chromatographically [Method 19]. This gave 13 mg (6% of theory) of the target compound.

Provenance & Evidence