Ethanolamine → [2-(2-Hydroxyethylamino)-2-oxoethoxy]acetic acid

HRID 1659969Notes

Reaction equation

CS([O-])(=O)=O.[C:6]1(=[O:13])[O:12][C:10](=[O:11])[CH2:9][O:8][CH2:7]1.[NH2:14][CH2:15][CH2:16][OH:17]>>[OH:17][CH2:16][CH2:15][NH:14][C:10](=[O:11])[CH2:9][O:8][CH2:7][C:6]([OH:12])=[O:13]

Participants

Reactant 3

HCID 700Ethanolamine

HCID 782321,4-Dioxane-2,6-dione

HCID 85257Methanesulfonate

Product 1

HCID 20558836[2-(2-Hydroxyethylamino)-2-oxoethoxy]acetic acid

Procedure

methanesulfonate by (a) reacting diglycolic anhydride and 2-aminoethanol to produce [2-(2-hydroxyethylamino)-2-oxoethoxy]acetic acid, (b) heating to cyclixe the latter to obtain 4-(2-hydroxyethyl)-3,5-dioxomorpholine, (c) esterifying the latter with methanesulfonyl chloride to produce 2-(3,5-dioxomorpholino)ethyl methanesulfonate and (d) reacting the mesylate with piperidine.

Sources & evidence

ORD record: ord-b5f7cf50a1f44b7180c07af8a790a63e
Source dataset: uspto-grants-1981_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04306063

Reaction notes

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