Water → HCID 22850139, compound

HRID 1198812Notes

Reaction equation

HRID 1198812 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 22850135HCID 22850135, compound

Product 1

HCID 22850139HCID 22850139, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3.32 g of isobutyl P-[2(S)-hydroxy-3-tosyloxy-propyl]-P-methyl-phosphinate and 1.19 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(S)-hydroxy-propyl]-P-methyl-phosphinate as a viscous oil, 31P-NMR spectrum: δ=+54.8 and +53.7 ppm (CDCl3), [α]D25 =+18.6 (0.56% 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-5392be8d4545460495f04824d99641a4
Source dataset
uspto-grants-1994_01
Patent number
US05281747

Reaction notes

Loading…