Reaktion #567854

Reaktionsgleichung

methyl 5-amino-3-(methoxycarbonyl)benzoate

diisopropylethylamine

p-toluoyl chloride

diisopropylethylamine

p-toluoyl chloride

→

desired compound

Ausbeute 99.0%

Methyl 3-(Methoxycarbonyl)-5-[(4-methylphenyl)carbonylamino]benzoate

Ausbeute 99.0%

Lösungsmittel

chloroform

chloroform

chloroform

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONAfter an addition 30 min
2. 2
   Sonstigethe volatiles were removed by rotary evaporation
3. 3
   workup.DISSOLUTIONthe resulting residue was dissolved in ethyl acetate
4. 4
   Extraktionextracted with 0.1 N aqueous NaOH
5. 5
   Extraktionfollowed by extraction with water
6. 6
   TrocknenThe organic layer was dried (MgSO4)
7. 7
   Filtrationfiltered
8. 8
   Sonstigevolatiles removed in vacuo

Vorschrift

To 1.20 g (5.74 mmol) of methyl 5-amino-3-(methoxycarbonyl)benzoate, compound 87, suspended in 50 mL of chloroform and 1.05 mL (6.00 mmol) of diisopropylethylamine was added 836 μL (6.32 mmol) of p-toluoyl chloride in 10 mL of chloroform over 30 min. The reaction was allowed to stir at ambient temperature for 2 hr. Then, another 100 μL (0.60 mmol) of diisopropylethylamine and 100 μL (0.76 mmol) of p-toluoyl chloride in 2 mL of chloroform was added. After an addition 30 min, the volatiles were removed by rotary evaporation and the resulting residue was dissolved in ethyl acetate and extracted with 0.1 N aqueous NaOH followed by extraction with water. The organic layer was dried (MgSO4), filtered, and volatiles removed in vacuo. This provided 1.86 g (5.68 mmol) of the desired compound. The product was identified by 1H NMR and mass spectroscopy and purity was assessed by RP-HPLC.

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