반응 #1834613

반응 방정식

Na2CO3

1-(2-Bromo-ethyl)-3-(4-methyl-benzo[b]thiophen-3-ylmethyl)-1,3-dihydro-benzimidazol-2-one

Methoxycarbonylmethyl-ammonium chloride

Et3N

Methoxycarbonylmethyl-ammonium chloride

Et3N

Na2CO3

→

{2-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-ethylamino}-acetic acid methyl ester

수율 98.0%

용매

CH3CN

water

반응 조건

후처리

1. 1
   workup.ADDITIONare added
2. 2
   workup.STIRRINGthe mixture is stirred at room temperature for another 48 hr
3. 3
   온도The mixture is then heated at 80° C. for 20 hrs
4. 4
   추출the mixture is extracted with EtOAc (3×15 mL)
5. 5
   기타dried
6. 6
   농축concentrated
7. 7
   기타to give crude product
8. 8
   기타Purification by flash column chromatography

실험 절차

1-(2-Bromo-ethyl)-3-(4-methyl-benzo[b]thiophen-3-ylmethyl)-1,3-dihydro-benzimidazol-2-one (30 mg, 0.075 mmol) is dissolved in CH3CN (0.5 mL)) and Methoxycarbonylmethyl-ammonium chloride (11 mg, 0.09 mmol) and Et3N (0.025 mL, 0.18 mmol) are added. The mixture is first stirred at room temperature for 16 hr. And then 11 mg of Na2CO3 is added and the mixture is stirred at room temperature for another 48 hr. Since the reaction is not completed, another 11 mg of Methoxycarbonylmethyl-ammonium chloride, 0.025 mL of Et3N and 11 mg of Na2CO3 are added. The mixture is then heated at 80° C. for 20 hrs. Then 10 mL of water is added and the mixture is extracted with EtOAc (3×15 mL). The organic layers are combined, dried and concentrated to give crude product. Purification by flash column chromatography affords 30 mg (98%) of {2-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-ethylamino}-acetic acid methyl ester.

출처