Lithium Hydroxide → HCID 11014769, compound

Participants

Reaction Steps

To a stirred solution of N-[(2-adamantyloxy)carbonyl]-α-methyl-D-tryptophan methyl ester (1.36 g, 3.3 mmol) in aqueous 1,4-dioxan (1:2) (20 mL) was added an excess of LiOH (0.210 g, 5 mmol) and stirred at room temperature overnight. After removing the solvent in vacuo the residue was chromatographed using 5% MeOH: 95% CH2Cl2 then 10% MeOH: 90% CH2Cl2 as eluants to yield the acid (0.953 mg, 90%) as a white solid, crystallized from n-hexane, mp 210°-215° C. (EtOAc/n-hexane); IR (film) 1689 cm-1 ; NMR (CDCl3 -D2O), δ1.3-2.2 (14H, m), 1.70 (3H, s), 3.26 (1H, d, J 13.5 Hz), 3.63 (1H, d, 13.5 Hz); 4.77 (1H, br.s), 6.85-7.60 (5H, m).

Provenance & Evidence