Benzyl chloroformate → HCID 53808165, compound

Participants

Reaction Steps

To 30 g (166 mmol) of (S)-6-aminoheptanoic acid hydrochloride in 57 ml of water are added 57 ml of 4N aqueous sodium hydroxide solution and thereafter dropwise simultaneously at 10° 92 ml of 4N aqueous sodium hydroxide solution and 42 ml (294 mol) of benzyl chloroformate so that the pH value always lies between 10 and 12. After the precipitation of the product the mixture is stirred at 0° for a further 2 hours. Thereafter, 300 ml of water are added and the reaction mixture is extracted with ether. The aqueous phase is then acidified with 20 ml of concentrated hydrochloric acid and extracted with methylene chloride. The methylene chloride phase is dried over magnesium sulphate and evaporated. The crystals obtained are recrystallized from chloroform/hexane, whereby there are obtained 33.1 g (72%) of (S)-6-[1-(benzyloxy)formamido]heptanoic acid, m.p. 82°-83°.

Provenance & Evidence