Potassium Carbonate → 6-(2-Chlorobenzyloxy)-4-methoxymethyl-beta-carboline-3-carboxylic acid isopropyl ester

HRID 36332

반응식

HRID 36332 반응식
[CH:1]([O:4][C:5]([C:7]1[N:8]=[CH:9][C:10]2[NH:11][C:12]3[C:17]([C:18]=2[C:19]=1[CH2:20][O:21][CH3:22])=[CH:16][C:15]([OH:23])=[CH:14][CH:13]=3)=[O:6])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[Cl:30][C:31]1[CH:38]=[CH:37][CH:36]=[CH:35][C:32]=1[CH2:33]Cl>C(O)(C)C>[CH:1]([O:4][C:5]([C:7]1[N:8]=[CH:9][C:10]2[NH:11][C:12]3[C:17]([C:18]=2[C:19]=1[CH2:20][O:21][CH3:22])=[CH:16][C:15]([O:23][CH2:33][C:32]1[CH:35]=[CH:36][CH:37]=[CH:38][C:31]=1[Cl:30])=[CH:14][CH:13]=3)=[O:6])([CH3:3])[CH3:2]

참가 물질

5

반응물 3

HCID 11430Potassium Carbonate2회HCID 119062-Chlorobenzyl chlorideHCID 153632686-Hydroxy-4-methoxymethyl-beta-carboline-3-carboxylic acid isopropyl ester

생성물 1

HCID 540020496-(2-Chlorobenzyloxy)-4-methoxymethyl-beta-carboline-3-carboxylic acid isopropyl ester수율 24.5%

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

A solution is prepared from 500 mg (1.6 mmol) of 6-hydroxy-4-methoxymethyl-β-carboline-3-carboxylic acid isopropyl ester in 50 ml of isopropanol, combined with 500 mg (3.6 mmol) of anhydrous, pulverized potassium carbonate, and stirred under argon for 10 minutes. Then 0.25 ml (1.99 mmol) of 2-chlorobenzyl chloride is added and the mixture refluxed for 2 hours. After suctioning off from the potassium carbonate, the filtrate is concentrated and separated over silica gel with methylene chloride:acetone=3:1 as the eluent, thus producing 172 mg of 6-(2-chlorobenzyloxy)-4-methoxymethyl-β-carboline-3-carboxylic acid isopropyl ester, mp 135°-141° C.

후처리

  1. temperaturethe mixture refluxed for 2 hours
  2. concentrationthe filtrate is concentrated
  3. customseparated over silica gel with methylene chloride

출처 및 근거

ORD 기록
ord-6d26eb94f6a3435093093fbd1d0857f1
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05414002

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