1-Hydroxybenzotriazole → benzyl N-[4-[[[2-(2,6-difluoro-4-hydroxyphenyl)-2-ethoxyacetyl]amino]methyl]benzenecarboximidoyl]carbamate

Participants

Reaction Steps

(RS)-(2,6-Difluoro-4-hydroxy-phenyl)-ethoxy-acetic acid (2.3 g) was dissolved in DMF (75 ml) and [(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] (3.18 g) and HOBt (2.15 g) were successively added. The slurry was cooled in an ice bath and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (3.05 g) was added. Et3N (8.0 ml) was slowly added. The resulting mixture was left to stir over night warming up to rt. After removing the solvent precipitation from CH2Cl2/MeOH 19:1 yielded the product. Drying over night on the high vacuum afforded 3.0 g (60 g) of pure (RS)-[(4-{[2-(2,6-difluoro-4-hydroxy-phenyl)-2-ethoxy-acetylamino]-methyl}-phenyl)-imino-methyl]-carbamic acid benzyl ester. White solid. MS 498.3 ([M+H]+).

Provenance & Evidence