Triethylamine → HCID 58116472, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 7.00 g (23.4 mmol) of the compound from Example 62A in concentrated acetic acid (150 ml) was admixed with 3.00 g of palladium/carbon (10% palladium) and 5.50 g of platinum(IV) oxide and then hydrogenated under a hydrogen atmosphere at standard pressure until conversion is complete. The reaction solution was filtered through Celite, the filter residue was washed with methanol/water and the combined filtrates were concentrated under reduced pressure. The residue (10.5 g) was taken up in dichloromethane (315 ml) and then admixed with 18.2 ml (13.2 g, 131 mmol) of triethylamine, and then admixed at 0° C. with 5.86 g (29.1 mmol) of 4-nitrophenyl chloroformate. The mixture was stirred at 0° C. for 2 h, then warmed to RT and stirred overnight. The reaction solution was washed with saturated aqueous sodium hydrogencarbonate solution and water, and the organic phase was dried over magnesium sulphate, filtered and concentrated under reduced pressure. The residue was purified by means of preparative HPLC and the title compound was thus obtained as a by-product. Yield: 1.32 g (14% of theory, purity 85%)

Provenance & Evidence