Acetic Acid → 2-[Bis-(2-hydroxy-ethyl)-amino]-4-chloro-6-methyl-10,10-dioxo-10,11-dihydro-5-oxa-10lambda *6*-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid methyl ester

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Reaction Conditions

Reaction Steps

Ethylene oxide (40 mL) was added to a mixture of the ester of Example 35j (1 g, 2.72 mmol), acetic acid (15 mL) and water (15 mL) at 0-5° C. THF (2 mL) was added and the reaction mixture was stirred at 0-5° C. for 4 h and then left for overnight at room temperature. It was treated with water and aqueous Na2CO3 solution to neutral pH followed by extraction with ethyl acetate. The organic layer was washed with water, brine, dried, concentrated and purified using flash chromatography (silica gel) to obtain the title compound. Yield: 0.9 g, (73%); 1H NMR (DMSO-d6): δ 2.8 (s, 3H, CH3), 3.6 (t, 4H, 2CH2), 3.7, (t, 4H, 2CH2), 3.9, (s, 3H, OCH3), 5.2, (s, 2H, CH2) 6.9, (s, 2H, Ar), 8.2 (s, 2H, Ar); MS: m/e (CI+) 455 (M+1).

Provenance & Evidence