1-Amino-2-propanol → 2-Propanol, 1-amino-, 2-(hydrogen sulfate)

HRID 2216231

Reaction equation

HRID 2216231 reaction equation
[NH2:1][CH2:2][CH:3]([OH:5])[CH3:4].[S:6](=O)(=[O:9])([OH:8])[OH:7]>>[S:6]([OH:9])([O:5][CH:3]([CH3:4])[CH2:2][NH2:1])(=[O:8])=[O:7]

Participants

3

Reactant 2

HCID 41-Amino-2-propanolHCID 1118Sulfuric Acid

Product 1

HCID 989852-Propanol, 1-amino-, 2-(hydrogen sulfate)

Procedure

FIG. 7 shows another synthetic reaction scheme for preparation of an mPEG-DTB-ligand compound in accord with the invention. The details of the reaction procedure are given in Examples 4A-4B. Briefly, cold 1-amino-2-propanol was reacted with sulfuric acid to form 2-amino-1methylethyl hydrogen sulfate. This product was reacted with carbon disulfide and sodium hydroxide in aqueous ethanol to yield 5-methylthiazolidine-2-thione. An aqueous solution of hydrochloric acid was added to the 5-methylthiazolidine-2-thione and heated. After refluxing for one week, the product, 1-mercapto(methyl)ethyl ammonium chloride, was crystallized and recovered. This product was reacted with methoxy carbonylsulfenyl chloride to yield 2-(methoxycarbonyldithio)ethaneamine. Reaction of the 2-(methoxycarbonyldithio)ethaneamine with mPEG-chloroformate using the procedure described above with respect to FIG. 4 yields the desired mPEG-DTB-nitrophenyl compound suitable for reaction with a selected amine-containing lipid.

Workup

  1. customanother synthetic reaction scheme
  2. customThe details of the reaction procedure

Sources & evidence

ORD record
ord-b7e08f1810814266b06d2d5ec6a49e49
Source dataset
uspto-grants-2006_09
Patent number
US07112337B2

Linked notes

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