Ethyl Glycolate → 3,11-Dioctyl-2,12-dioxo-7-sulfoethyl-3,7,11-triaza-1, 5,9,13-tridecanetetraol

HRID 1269

Reaction equation

[OH:1][CH:2]([CH2:13][N:14]([CH2:28][CH2:29][S:30]([OH:33])(=[O:32])=[O:31])[CH2:15][CH:16]([OH:27])[CH2:17][NH:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:3][NH:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[C:34]([O:38]CC)(=O)[CH2:35][OH:36]>C1(C)C=CC=CC=1>[CH2:5]([N:4]([CH2:3][CH:2]([OH:1])[CH2:13][N:14]([CH2:28][CH2:29][S:30]([OH:33])(=[O:31])=[O:32])[CH2:15][CH:16]([OH:27])[CH2:17][N:18]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C:35](=[O:36])[CH2:34][OH:38])[C:35](=[O:36])[CH2:34][OH:38])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

Conditions

Temperature: 100 °C

Procedure

A reactor was charged with 10 g (0.02 mole) of 11,15-dihydroxy-13-sulfoethyl-9,13,17-triazapentacosane, 50 ml of toluene and 5.1 ml (0.05 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→20/1), thereby obtaining 10.6 g (isolation yield: 91%) of 3,11-dioctyl-2,12-dioxo-7-sulfoethyl-3,7,11-triaza-1, 5,9,13-tridecanetetraol.

Workup

customwhile purging ethanol
customformed with a nitrogen stream
customAfter completion of a reaction
distillationthe solvent was distilled off under reduced pressure
customthe residue was purified by column chromatography (on 200 g of silica gel, developing solvent: chloroform/methanol=100/1→20/1)

Sources & evidence

ORD record: ord-7c6c206c7c6b448dac5969421cf30787
Source dataset: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05723655

Linked notes

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