1-Hydroxybenzotriazole → Benzyl carbamate

Participants

Reaction Conditions

Reaction Steps

(RS)-[2,6-Difluoro-4-(4-methoxy-phenoxy)-phenyl]-ethoxy-acetic acid (398 mg) was dissolved in DMF (15 ml). [(4-aminomethyl-phenyl)-imino-methyl]-carbamic acid benzyl ester dihydrochloride [Prepared according to Ch. Lila, Ph. Gloanec, L. Cadet, Y. Hervé, J. Fournier, F. Leborgne, T. J. Verbeuren, G. De Nanteuil, Synthetic Communications 1998, 28, 23, 4419–4429] (367 mg) and 1-hydroxybenzotriazole (254 mg) were added and the mixture was cooled to 0° C. N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (254 mg) and triethylamine (1.38 ml) were added and it was stirred 1 h at 0° C. and 5.5 h at rt. The solvent was evaporated and the residue was taken up in H2O (40 ml) and CH2Cl2 (30 ml). The organic layer was separated, washed with brine and dried (MgSO4). The aqueous layers were extracted with two more portions CH2Cl2. After evaporation of the solvent CC(CH2Cl2 to CH2Cl2/MeOH 98:2) afforded 228 mg (32%) of (RS)-[4-(12-[2,6-difluoro-4-(4-methoxy-phenoxy)-phenyl]-2-ethoxy-acetylamino)-methyl)-phenyl]-imino-methyl}-carbamic acid benzyl ester. White foam. MS 602.0 ([M−H]−).

Provenance & Evidence