Beta-Alanine → N-Benzyloxycarbonyl-beta-alanine

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Reaction Steps

6.0 g of β-alanine are taken up in 33.7 ml of 2N NaOH and cooled to +5°. At this temperature there are then added dropwise, simultaneously, 22.5 ml of a 50% solution of chloroformic acid benzyl ester in toluene and 16.8 ml of 4N NaOH. The emulsion is subsequently stirred in an ice bath for 3 hours. After separating off the organic phase, the aqueous phase is extracted once more with ether and then, while cooling with an ice bath, the pH is adjusted to 1 with 44 ml of 2N HCl. By filterirg off the precipitate and drying in a high vacuum at 50°, Z-β-Ala-OH is obtained in the form of a white powder; Rf (CH2Cl2 /MeOH/concentrated aqueous ammonia solution [5:3:1])=0.37.

Provenance & Evidence