Ammonia → HCID 14843568, compound

HRID 373899Notes

Reaction equation

HRID 373899 reaction equation
C([O:4][CH2:5][CH:6]([CH2:17][O:18]C(=O)C)[CH2:7][CH2:8][P:9](=[O:16])([O:13][CH2:14][CH3:15])[O:10][CH2:11][CH3:12])(=O)C.N>Cl.C(O)C.O1CCCC1>[OH:4][CH2:5][CH:6]([CH2:17][OH:18])[CH2:7][CH2:8][P:9](=[O:16])([O:10][CH2:11][CH3:12])[O:13][CH2:14][CH3:15]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 19027595HCID 19027595, compound

Product 1

HCID 14843568HCID 14843568, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21887872Ethanol hydrochlorideSolvent

Conditions

Temperature
80 °C

Procedure

Diethyl 4-acetoxy-3-(acetoxymethyl)butylphosphonate (4.6 g, 14.18 mmol) was dissolved in hydrochloric acid/ethanol solution (14 ml, 2.2M) and the reaction mixture was stirred at 80° C. for 90 minutes. It was then cooled to 5° C., neutralized with aqueous ammonia solution and diluted with tetrahydrofuran. The resulting ammonium hydrochloride was filtered off, washed with tetrahydrofuran and the combined filtrates concentrated to an oil which was chromatographed on silica gel (eluting with 94:6 CHCl3 :EtOH) to give the title compound (2.1 g, 62%). 1H NMR δH ](CD3)2SO] 1.22 (6H, t, 7=7Hz, (OCH2CH3)2), 1.46 (3H, m, CH2CH) 1.72 (2H, m, PCH2), 3.35 (4H, m, 2xH2OH), 3.5-3.75 (2H, br.s, D2O exchangeable, 2xOH), 3.96 (4H, m, (OCH2CH3)2). Found: C,44.79: H,8.93%. C9H21O5P 0.2 H2O requires: C,44.43; H,8.86.

Workup

  1. temperatureIt was then cooled to 5° C.
  2. filtrationThe resulting ammonium hydrochloride was filtered off
  3. washwashed with tetrahydrofuran
  4. concentrationthe combined filtrates concentrated to an oil which
  5. customwas chromatographed on silica gel (eluting with 94:6 CHCl3 :EtOH)

Sources & evidence

ORD record
ord-de3a8f3636fe4b4890788319a7e90a73
Source dataset
uspto-grants-1992_11
Patent number
US05166198

Reaction notes

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