L-Tyrosine → HCID 11439483, compound

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Reaction Steps

The first step (a) is the bis-protection of tyrosine amino acid using allyl chloroformate, as described in Stevens, C. M. and Watanabe, R., J. Am. Chem. Soc., 1950, 72, 725-727 (FIG. 11A). Tyrosine (n=0.03 mol, m=5.44 g) is dissolved in 15 ml of 4N sodium hydroxide and treated, when cold, with 7.02 ml (2.2 equiv.) of allyl chloroformate and additional 15 ml of 4N sodium hydroxide. After treatment and purification, O,N-dicarboallyloxy-L-tyrosine is obtained in 89% yield (Litt. 91%) as a crystalline derivative.

Provenance & Evidence