Stearoyl chloride → HCID 69114586, compound

Participants

Reaction Conditions

Reaction Steps

1.33 g. of N-hydroxy succinimide (11.56 mmole) and DIEA (1.5 ml, 8.62 mmole) were dissolved in 50 ml of anhydrous THF and gently stirred at 0° C. under nitrogen atmosphere. To this were added dropwise and during 1 h a solution of stearoyl chloride (2.35 g, 7.7 mmole) in 50 ml of anhydrous THF. After, the mixture was stirred at 0° C. for 2 h and overnight at room temperature. Solvent was removed under reduced pressure and the remaining white solid was redissolved in 200 ml of DCM. The organic phase were washed with DDW (2×100 ml), dried over anhydrous MgSO4, filtered and evaporated to dryness. The reaming solid was dissolved in 100 ml of ethyl acetate and 200 ml of hexane and kept at −20° C. overnight. The resulting white crystals were collected by filtration and dried in vacuum over NaOH-pellets. The crystallized product was free from unreacted acid chloride as determined by 1H-NMR. The remaining filtrate was also evaporated to yield the product contaminated with 10% of the starting acid as determined by 1H-NMR.

Provenance & Evidence