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

HRID 1940530Notes

Reaction equation

HRID 1940530 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-9ceb462f88494136a8bbde330671af8e
Source dataset
uspto-grants-1997_12
Patent number
US05700808

Reaction notes

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