Formaldehyde → 3-[3-[3-[(3,4-dichlorophenyl)methyl-methyl-carbamoyl]-4-hydroxy-5-oxo-2H-pyrrol-1-yl]propanoylamino]propanoic acid

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

A mixture of paraformaldehyde (0.015 g, 0.5 mmol) and methanol (1.5 mL) was warmed to 55° C. Added to this mixture was H-β-Ala-β-ala-OH (0.08 g, 0.5 mmol) and the solution was stirred 5 min. N-(3,4-Dichloro-benzyl)-2-(2,2-dimethyl-5-oxo[1,3]dioxolane-4-ylidene)-N-methyl-acetamide (0.1715 g, 0.5 mmol) was added and the mixture was stirred at 55° C. for 45 min. The mixture was concentrated and the resulting residue was triturated with ethylacetate and filtered to give the desired product as a white solid (0.0358 g, 16% yield). 1H NMR (300 MHz, DMSO) δ: 2.35 (t, J=6.7 Hz, 4H), 2.96 (s, 3H), 3.32 (m, 2H), 3.57 (m, 2H), 4.02 (s, 2H), 4.57 (s, 2H), 7.23 (d, J=6.6 Hz, 1H), 7.51 (s, 1H), 7.61 (d, J=8.4 Hz, 1H), 8.05 (t, J=10.3 Hz, 1H), 10.97 (s, 1H), 12.19 (s, 1H). HRMS (M+H) calcd for C19H21N3Cl2O6: 456.07292. found: 456.0738.

Herkunft & Nachweise