Réaction #46296

Équation de réaction

tert-butyl[11-(3-chloro-4-fluorobenzyl)-9-methoxy-1,8,10-trioxo-1,3,4,5,6,8,10,11,12,13-decahydro-2H-[1,4]diazocino[2,1-a]-2,6-naphthyridin-2-yl]acetate

hydrogen bromide

→

title compound

[11-(3-Chloro-4-fluorobenzyl)-9-hydroxy-1,8,10-trioxo-1,3,4,5,6,8,10,11,12,13-deca-hydro-2H-[1,4]diazocino[2,1-a]-2,6-naphthyridin-2-yl]acetic acid

Solvants

acetic acid

dioxane

Conditions de réaction

Traitement

1. 1
   ConcentrationThe product mixture was concentrated under vacuum
2. 2
   Lavageeluted with a 95-5% water-acetonitrile gradient
3. 3
   AutreCollection and lyophilization of appropriate fractions

Mode opératoire

A mixture of tert-butyl[11-(3-chloro-4-fluorobenzyl)-9-methoxy-1,8,10-trioxo-1,3,4,5,6,8,10,11,12,13-decahydro-2H-[1,4]diazocino[2,1-a]-2,6-naphthyridin-2-yl]acetate (50 mg, 0.09 mmol) and 33% hydrogen bromide in acetic acid (1 mL) in dioxane (1 mL) was stirred at room temperature for 1 hour. The product mixture was concentrated under vacuum. The residue was subjected to reverse phase column chromatography on C-18 stationary phase eluted with a 95-5% water-acetonitrile gradient. Collection and lyophilization of appropriate fractions afforded the title compound. 1H NMR (400 MHz, CDCl3) δ 7.34 (dd, J=6.6, 2.1 Hz, 1H), 7.18 (br signal, 1H), 7.11 (t, J=8.4 Hz, 1H), 4.78 (d, J=14.8 Hz, 1H), 4.52 (d, J=14.8 Hz, 1H), 4.41 (d, J=17.8 Hz, 1H), 4.07 (d, J=17.8 Hz, 1H), 3.67 (m, 1H), 3.51-3.36 (m), 3.23 (br d, 1H), 2.96 (m), 2.60 (m, 1H), 2.08 (m), 1.96 (m), 1.76 (m). (ES MS M+1=478.2)

Source