1-Hydroxybenzotriazole → HCID 437008, compound

Participants

Reaction Steps

A solution of 0.165 g of 2(R)-[1(S)-(carboxy)-4-phenylbutyl]-2′-(methanesulphonyl)-4-methyl-2′-phenylvalerohydrazide in 4 ml of dry dimethylformamide was cooled to 0° C. while stirring under nitrogen and 0.09 g of 1-hydroxybenzotriazole and 0.09 g of 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride were added in succession. After stirring for 40 minutes at 0° C. the solution was treated with 0.18 g of 0-(tert-butyldimethylsilyl)hydroxylamine and the mixture was left to come to room temperature and then stirred overnight. The solvent was evaporated and the residue was partitioned between ethyl acetate and 5% aqueous sodium hydrogen carbonate solution. The ethyl acetate layer was washed in succession with water, 2M sulphuric acid, water and brine and then dried over anhydrous magnesium sulphate. The solvent was evaporated to give a pale pink gum which on crystallization from ether gave 0.05 g of 2(R)-[1(S)-(hydroxycarbamoyl)-4-phenylbutyl]-2′-methanesulphonyl)-4-methyl-2′phenylvalerohydrazide in the form of an off-white solid.

Provenance & Evidence