Ethanol → HCID 18980720, compound

HRID 2392921Notes

Reaction equation

[CH2:1]([N:5]([CH2:19][CH:20]([OH:31])[CH2:21][NH:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH2:6][CH:7]([OH:18])[CH2:8][NH:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:2][CH2:3][CH3:4].[OH2:32].Cl[CH2:34][C:35]([O-:37])=[O:36].[Na+].[CH2:39]([OH:41])[CH3:40]>>[CH2:1]([N:5]([CH2:19][CH:20]([OH:31])[CH2:21][N:22]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH2:40][C:39]([OH:32])=[O:41])[CH2:6][CH:7]([OH:18])[CH2:8][N:9]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:34][C:35]([OH:37])=[O:36])[CH2:2][CH2:3][CH3:4]

Participants

Reactant 4

HCID 702Ethanol2×

HCID 962Water

HCID 18980718HCID 18980718, compound

HCID 23665759Sodium chloroacetate

Product 1

HCID 18980720HCID 18980720, compoundYield 85%

Conditions

Temperature: 70 °C

Procedure

A reactor was charged with 18.6 g (0.04 mole) of 13-butyl-11,15-dihydroxy-9,13,17-triazapentacosane, 100 g of ethanol and 50 g of water, and the contents were heated to 70° C. Thereafter, an aqueous solution of 43 g (0.37 mole) of sodium chloroacetate was added to the contents. The resultant mixture was kept at pH 9 and stirred for 20 hours. After completion of the reaction, ethanol was distilled off under reduced pressure, and the residue was diluted to 10% with water. The resulting solution was adjusted to pH 7, desalted by electrodialysis and lyophilized, thereby obtaining 20.2 g (isolation yield: 85%) of 6-butyl-4,8-dihydroxy-2,10-dioctyl-2,6,10-triaza-1,11-undecanedicarboxylic acid.

Workup

distillationwas distilled off under reduced pressure
additionthe residue was diluted to 10% with water

Sources & evidence

ORD record: ord-b029c0c5c4734c518bc68ed37a1b4387
Source dataset: uspto-grants-1998_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05801270

Reaction notes

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