Diethyl Ether → HCID 131713411, compound

HRID 1903120Notes

Reaction equation

HRID 1903120 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[C:16]([C:17]=2[CH:18]=1)=[CH:15][C:14]([C:19]#[C:20][CH2:21]Cl)=[CH:13][CH:12]=3)=[O:5])[CH3:2].CCOCC.[CH2:28]([O:30][P:31]([O:35]CC)[O:32][CH2:33][CH3:34])[CH3:29]>>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[C:16]([C:17]=2[CH:18]=1)=[CH:15][C:14]([C:19]#[C:20][CH2:21][P:31]([O:32][CH2:33][CH3:34])([O:30][CH2:28][CH3:29])=[O:35])=[CH:13][CH:12]=3)=[O:5])[CH3:2]

Participants

4

Reactant 3

HCID 3283Diethyl EtherHCID 31215Triethyl phosphiteHCID 13136250HCID 13136250, compound

Product 1

HCID 131713411HCID 131713411, compound

Procedure

460 mg of 6-(3-chloro-1-propinyl)-beta-carboline-3-carboxylic-acid-ethylester is stirred in 4 ml of triethylphosphite for 3 h at 120°-130° C. The mixture, after being cooled, is thoroughly stirred with ether and the ether-soluble part is chromatographed after evaporation on 50 g of silica gel using methylene-chloride/ethanol (10/2). 105 mg of 6-[3-diethoxyphosphoryl-1-propinyl]beta-carboline-3-carboxylic-acid-ethylester is obtained in the form of an oil.

Workup

  1. temperatureThe mixture, after being cooled
  2. customthe ether-soluble part is chromatographed
  3. customafter evaporation on 50 g of silica gel

Sources & evidence

ORD record
ord-24ec7ad182c4480d8f9aa9f7a8ae1530
Source dataset
uspto-grants-1984_03
Patent number
US04435403

Reaction notes

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