Water → HCID 22850138, compound

HRID 2210770Notes

Reaction equation

HRID 2210770 reaction equation
[OH:1][C@H:2]([CH2:12]OS(C1C=CC(C)=CC=1)(=O)=O)[CH2:3][P:4]([CH3:11])(=[O:10])[O:5][CH2:6][CH:7]([CH3:9])[CH3:8].[N-:24]=[N+:25]=[N-:26].[Na+].O>CN(C)C=O>[N:24]([CH2:12][C@@H:2]([OH:1])[CH2:3][P:4]([CH3:11])(=[O:10])[O:5][CH2:6][CH:7]([CH3:9])[CH3:8])=[N+:25]=[N-:26]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 22850134HCID 22850134, compound

Product 1

HCID 22850138HCID 22850138, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4.3g of isobutyl P-[2(R)-hydroxy-3-tosyloxy-propyl]-P-methyl-phosphinate and 1.5 g of sodium azide in 25 ml of dry dimethylformamide is heated to a temperature of 120° for a period of 3 hours under an inert gas atmosphere. The reaction mixture is allowed to cool to room temperature, poured onto 50 ml of water and extracted twice with 100 ml of ethyl acetate. The organic extract is dried over magnesium sulphate and the solvent removed under reduced pressure. The residue is chromatographed on silica gel using 5 parts of ethyl acetate to 1 part of ethanol as eluent. There is obtained isobutyl P-[3-azido-2(R)-hydroxy-propyl]-P-methyl-phosphinate as a viscous oil, 31P-NMR spectrum: a δ=+54.8 and +53.7 ppm (CDCl3), [α]D25 =-15.8(0.51% in ethanol).

Workup

  1. extractionextracted twice with 100 ml of ethyl acetate
  2. extractionThe organic extract
  3. dry with materialis dried over magnesium sulphate
  4. customthe solvent removed under reduced pressure
  5. customThe residue is chromatographed on silica gel using 5 parts of ethyl acetate to 1 part of ethanol as eluent

Sources & evidence

ORD record
ord-fe5819e96d034064b2c7ca088619f189
Source dataset
uspto-grants-1995_10
Patent number
US05461040

Reaction notes

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