Methane → O-benzyl-L-tyrosine

Participants

Reaction Conditions

Reaction Steps

HO-Tyr(Bzl)-NH2 (20.0 g, 105.7 mmol) was suspended in 300 mL of anhydrous THF and heated to 50° C. Phosgene (20% in toluene) (73.7 mL, 147.4 mmol) was added the amino acid suspension. The amino acid dissolved over the course of approx. 1 hr, forming a pale yellow solution. The solution was concentrated on the rotovap, transferred to a beaker, and hexane was added to precipitate the product. The off-white solid was isolated by filtration and dissolved in anhydrous THF. The solution was stirred over carbon black and subsequently filtered over a bed of Celite. An excess of hexane was added to the filtrate to precipitate the product. The NCA was isolated by filtration and dried in vacuo. 14.3 g (65% yield) of Tyr(Bzl) NCA was isolated as a off-white, solid. 1H NMR (d6-DMSO) δ 9.07 (1H), 7.49-7.29 (5H), 7.12-7.07 (2H), 6.98-6.94 (2H), 5.06 (2H), 4.74 (1H), 3.05-2.88 (2H) ppm.

Provenance & Evidence