5-Aminopentan-1-ol → 2-(5-Hydroxypentyl)amino-2-oxoethoxylacetic acid

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][CH2:17][CH2:18][CH2:19][OH:20]>>[OH:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][NH:14][CH:9]([O:8][CH2:7][CH:6]=[O:13])[C:10]([OH:12])=[O:11]

Participants

Reactant 3

HCID 756345-Aminopentan-1-ol

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

HCID 85257Methanesulfonate

Product 1

HCID 202858622-(5-Hydroxypentyl)amino-2-oxoethoxylacetic acid

Procedure

methanesulfonate by the following sequence of steps: (a) by reacting diglycolic anhydride and 5-aminopentanol to produce [2-(5-hydroxypentyl)amino-2-oxoethoxylacetic acid, (b) heating to cyclize the latter to obtain 4-(5-hydroxypentyl)-3,5-dioxomorpholine, (c) esterifying the latter with methanesulfonyl chloride to produce 5-(3,5-dioxomorpholino)pentyl methanesulfonate and (d) reacting the mesylate with 2-benzhydrylpiperidine.

Sources & evidence

ORD record: ord-144787c7592949a3b5fbc70ae64e01f9
Source dataset: uspto-grants-1981_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04256891

Reaction notes

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