Реакция #10052

Уравнение реакции

Triethylamine

methyl-3-(aminomethyl)-2-(methoxycarbonyl)benzoate hydrochloride

Benzyl chloroformate

→

product

Выход 76.0%

Methyl-3-[(benzyloxycarbonylamino)methyl]-2-(methoxycarbonyl)benzoate

Выход 76.0%

Растворители

dichloromethane

Условия реакции

Обработка

1. 1
   Другоеbetween 4–7° C
2. 2
   workup.ADDITIONAfter the addition
3. 3
   Температураwarmed to room temperature for 4 hours
4. 4
   ПромывкаThe mixture was washed with water (2×30 ml), brine (30 ml)
5. 5
   Другоеdried
6. 6
   ДругоеSolvent was removed
7. 7
   Другоеthe residue was purified by chromatography (dichloromethane/ethyl acetate 95 to 5)

Методика

Triethylamine (1.87 g, 18.5 mmol) was added to a stirred suspension of methyl-3-(aminomethyl)-2-(methoxycarbonyl)benzoate hydrochloride (2.0 g, 8 mmol) in dichloromethane (30 ml). The mixture was cooled in an ice bath to 4° C. Benzyl chloroformate (1.66 g, 10 mmol) was added slowly keeping the temperature between 4–7° C. After the addition was complete, the cooled mixture was stirred an additional 30 minutes and then warmed to room temperature for 4 hours. The mixture was washed with water (2×30 ml), brine (30 ml) and dried. Solvent was removed and the residue was purified by chromatography (dichloromethane/ethyl acetate 95 to 5) to give 2.1 g (76%) of the product as a solid; 1H NMR (CDCl3) δ 7.87 (d, J=7.8 Hz, 1H), 7.63 (d, J=7.6 Hz, 1H), 7.46 (t, J=7.7 Hz, 1H), 7.36–7.26 (m, 5H), 5.41 (b, 1H), 5.09 (s, 2H), 4.36 (d, J=6.3 Hz, 2H), 3.91 (s, 3H), 3.88 (s, 3H).

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