Methyl L-phenylalaninate hydrochloride → HCID 6999129, compound

Participants

Reaction Steps

Phenylalanine methyl ester hydrochloride (0.5 g, 2.3 mmol) was suspended in 10 mL of dry THF. Et3 n (0.35 mL, 2.5 mol) was added, after which both CBZ-Ala (10, 0.52 g, 100 mol %) and 1 (0.65 g, 104 mol %) were also added. The reaction mixture was stirred for 24 h at room temperature. Following the general procedure gave 21, 0.74 g, 84%, as a crystalline solid. An identical reaction using DMF as the solvent produced 21 in 93% yield: mp 97°-98° C.; [α]25D -8.3° (c 0.3, EtOH); 1H NMR δ 7.42-7.15 (m, 10H), 6.40 (d, 1H, J=4), 5.24-5.21 (m, 1H), 5.10 (s, 2H), 4.88-4.84 (m, 1H), 4.24-4.21 (m, 1H), 3.78 (s, 3H), 3.16-3.13 (m, 2H), 1.38 (d, 3H, J=7). Anal. Calcd for C21H24N3O5 : C, 65.5; H, 6.3,; N, 7.3. Found: C, 65.5; H, 6.3; N, 7.3. Compound 21 was also synthesized from the reaction of 11 and isourea 2 (R=M1) in DMF (82% yield) and was identical to material formed above.

Provenance & Evidence