Ethyl Glycolate → HCID 19702830, compound

HRID 861300Notes

Reaction equation

HRID 861300 reaction equation
[OH:1][CH:2]([CH2:17][NH:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH2:3][NH:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[C:31]([O:35]CC)(=O)[CH2:32][OH:33]>C1(C)C=CC=CC=1>[CH2:19]([N:18]([CH2:17][CH:2]([OH:1])[CH2:3][N:4]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[C:32](=[O:33])[CH2:31][OH:35])[C:32](=[O:33])[CH2:31][OH:35])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]

Participants

4

Reactant 2

HCID 12184Ethyl GlycolateHCID 19702820HCID 19702820, compound

Product 1

HCID 19702830HCID 19702830, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A reactor was charged with 10.7 g (0.03 mole) of 15-hydroxy-13,17-diazanonacosan, 50 ml of toluene and 7.1 ml (0.07 mole) of ethyl glycolate, and the contents were heated to 100° C. and continuously stirred for 7.5 hours while purging ethanol formed with a nitrogen stream. After completion of a reaction, the solvent was distilled off under reduced pressure, and the residue was purified by column chromatography (on 200 g of silica gel, developing solvent: chloroform/methanol=100/1), thereby obtaining 13 g (yield: 96%) of the title compound as a viscous liquid.

Workup

  1. customwhile purging ethanol
  2. customformed with a nitrogen stream
  3. customAfter completion of a reaction
  4. distillationthe solvent was distilled off under reduced pressure
  5. customthe residue was purified by column chromatography (on 200 g of silica gel, developing solvent: chloroform/methanol=100/1)

Sources & evidence

ORD record
ord-b246237f56884912b9732771fe574f5f
Source dataset
uspto-grants-1998_02
Patent number
US05714457

Reaction notes

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