반응 #57996

반응 방정식

Triethylamine

Methyl 4-(2-aminoethylsulfanyl)benzoate hydrochloride

benzofuran-2-carboxylic acid

HBTU

NaHCO3

→

methyl 4-{2-[(benzofuran-2-yl-carbonyl)-amino]ethylsulfanyl}benzoate

수율 38.8%

용매

DMF

반응 조건

후처리

1. 1
   기타to give
2. 2
   기타precipitates which
3. 3
   workup.ADDITIONwas broken up by the addition of water (20 ml)
4. 4
   여과The solid was filtered
5. 5
   workup.DISSOLUTIONthe cake was dissolved in ethyl acetate
6. 6
   기타The residual water was removed by pipette and hexane
7. 7
   workup.ADDITIONwas added

실험 절차

Methyl 4-(2-aminoethylsulfanyl)benzoate hydrochloride (0.248 g, 1.00 mmol), was combined with benzofuran-2-carboxylic acid (0.162 g, 1.00 mmol) and HBTU (0.379 g, 1.00 mmol) in DMF (5 ml) at room temperature. Triethylamine (0.307 ml, 2.2 mmol) was added and the reaction mixture was stirred at room temperature overnight. Saturated aqueous NaHCO3 (15 ml) was added to give precipitates which was broken up by the addition of water (20 ml). The solid was filtered and the cake was dissolved in ethyl acetate. The residual water was removed by pipette and hexane was added to give methyl 4-{2-[(benzofuran-2-yl-carbonyl)-amino]ethylsulfanyl}benzoate (0.138 g) as a gum which was used in the next step without further purification.

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