Ethyl orthoformate → HCID 59238170, compound

Participants

Reaction Steps

4-[4-Amino-3-(methoxycarbonylmethyl-carbamoyl)-phenyl]-[1,4]diazepane-1-carboxylic acid tert-butyl ester (30.6 g) was treated with 375 mL of triethylorthoformate at 125° C. with stirring for 18 hours. At this time, reaction mixture was concentrated in vacuo and the resulting residue was taken up in ethyl acetate and water. The organic phase was washed thrice with 10% KHSO4 aqueous solution, once with water, once with brine. The organic layer was then dried over magnesium sulfate and was filtered. The filtrate was concentrated in vacuo. The product was purified by flash column chromatography (500 g of silica) eluting with 60% to 70% ethyl acetate in hexane. Appropriate fractions were collected and evaporated to dryness. The resulting residue was dissolved in diethyl ether and re-evaporated; this dissolution and re-evaporated was repeated using pentane. All solids obtained as foams were pooled, resulting in a total yield of 15.56 g of 4-(3-methoxycarbonylmethyl-4-oxo-3,4-dihydro-quinazolin-6-yl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester.

Provenance & Evidence