반응 #42367

반응 방정식

diisopropylethylamine

HATU

5-aminolevulinic acid methyl ester hydrochloride

Methyl hydrogen isophthalate

→

title compound

Methyl 3-{[(5-methoxy-2,5-dioxopentyl)amino]carbonyl}benzoate

용매

DMF

methylene chloride

반응 조건

후처리

1. 1
   기타The reaction is partitioned between ethyl acetate and water
2. 2
   세척The organic layer is washed with 1 N hydrochloric acid, saturated sodium bicarbonate, and brine
3. 3
   건조dried (magnesium sulfate)
4. 4
   여과filtered
5. 5
   농축concentrated under reduced pressure
6. 6
   기타Purification by flash column chromatography (silica, 4% methanol/chloroform)

실험 절차

Methyl hydrogen isophthalate (1.8 g, 10.2 mmol) is dissolved in methylene chloride (10 mL) and DMF (10 mL), and diisopropylethylamine (4.4 mL, 25.5 mmol), HATU (4.6 g, 12.2 mmol), and 5-aminolevulinic acid methyl ester hydrochloride (2 g, 11.2 mmol) are added. The reaction stirred at room temperature 1 h. The reaction is partitioned between ethyl acetate and water. The organic layer is washed with 1 N hydrochloric acid, saturated sodium bicarbonate, and brine, dried (magnesium sulfate), filtered, and concentrated under reduced pressure. Purification by flash column chromatography (silica, 4% methanol/chloroform) provides the title compound. ESI MS m/z 306.1 [M−H]−.

출처