تفاعل #42367

معادلة التفاعل

diisopropylethylamine

HATU

5-aminolevulinic acid methyl ester hydrochloride

Methyl hydrogen isophthalate

→

title compound

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

المذيبات

DMF

methylene chloride

ظروف التفاعل

المعالجة

1. 1
   أخرىThe reaction is partitioned between ethyl acetate and water
2. 2
   غسيلThe organic layer is washed with 1 N hydrochloric acid, saturated sodium bicarbonate, and brine
3. 3
   تجفيفdried (magnesium sulfate)
4. 4
   ترشيحfiltered
5. 5
   تركيزconcentrated under reduced pressure
6. 6
   أخرىPurification by flash column chromatography (silica, 4% methanol/chloroform)

الإجراء التجريبي

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]−.

المصدر