Hydrochloric Acid → HCID 69753596, compound

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Reaction Steps

6.2 g of benzyl 4-azido-1-[3-(4-tert-butyloxycarbonylaminomethylphenyl)propionyl]prolinate (starting material B3) are dissolved in 50 ml of tetrahydrofuran, and 3.52 g of triphenylphosphine are then added a little at a time, as a result of which a clear evolution of gas can be observed. After 4 h of stirring at RT, 10 ml of water are added, and the mixture is stirred at RT for 6 days. 12.5 ml of 1N hydrochloric acid solution are added, and the mixture is then extracted twice with ethyl acetate. Using 13 ml of 1N sodium hydroxide solution, the aqueous phase is made slightly alkaline, and the phase is then extracted three times with a mixture of ether/methanol (8:2). The extract is dried over magnesium sulfate and then concentrated, and the residue is dried under high vacuum. This gives 2.22 g of the title compound as a viscous oil. The mass spectrum shows the molecular peaks MH+, MNa+ and M2H+ at 482, 504 and 962 Da, respectively.

Provenance & Evidence