Hydrochloric Acid → HCID 86759487, compound

Participants

Reaction Steps

Carbonyl di-imidazole (2.37 g, 14.6 mmol) was added to a stirring solution of (3aS,4S,6R,6aR)-6-[2-chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid (prepared by following the method of Preparation 4 in International Patent Application No. WO94/17090) (6.015 g, 11.23 mmol) in dry dichloromethane (30 ml) under nitrogen. Mixture was stirred for 1 h. A dichloromethane solution of N,O-dimethylhydroxylamine (25.8 mmol; generated by basification of a 10 ml aqueous solution of 2.57 g of the corresponding hydrochloride at 0° C. with aqueous sodium hydroxide, followed by extraction with 3×5 ml dichloromethane and dried over sodium sulphate) was added. Mixture was stirred at room temperature for 60 h, quenched with aqueous citric acid (10% w/v, 40 ml). Organic solution was separated, washed with aqueous sodium bicarbonate (8% w/v, 40 ml), dried (sodium sulphate) and filtered. Removal of solvent in vacuo gave the title compound as a creamy white foam (6.66 g). TLC (100% ethyl acetate, visualised under an UV lamp) rf=0.51.

Provenance & Evidence