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

HRID 36332

反応式

HRID 36332 の反応式
[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]

参加物

5

反応物 3

HCID 11430Potassium Carbonate2 回HCID 119062-Chlorobenzyl chlorideHCID 153632686-Hydroxy-4-methoxymethyl-beta-carboline-3-carboxylic acid isopropyl ester

生成物 1

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

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-6d26eb94f6a3435093093fbd1d0857f1
出典データセット
uspto-grants-1995_05
特許番号
US05414002

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