Hydrochloric Acid → HCID 21897905, compound

HRID 719252Notes

Reaction equation

HRID 719252 reaction equation
C([O:3][P:4]([C:9]([O:22]CC)([P:11]([O:19]CC)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:12])[CH3:10])(=[O:8])[O:5]CC)C.Cl.C(OP(C(O)(P(O)(C1C=CC=CC=1)=O)C)(=O)OCC)C>>[OH:22][C:9]([P:4](=[O:3])([OH:5])[OH:8])([P:11]([OH:19])([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:12])[CH3:10]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 86588252HCID 86588252, compoundHCID 86588253HCID 86588253, compound

Product 1

HCID 21897905HCID 21897905, compound

Conditions

Temperature
120 °C

Procedure

[1-Ethoxy-1-(ethoxy-phenyl-phosphinoyl)-ethyl]phosphonic acid diethyl ester (7c) (67 mg, 1.9 mmol) was combined with concentrated HCl (2 mL). The solution was heated to reflux (120° C.) for 20 hours. The following morning HPLC indicated that all [1-Hydroxy-1-(hydroxy-phenyl-phosphinoyl)-ethyl] phosphonic acid diethyl ester was gone. Excess HCl was removed under a stream of N2 at 100° C. The residue was placed on the high vac for further drying and then dissolved in 6 mL 1:1 CH3CN/H2O. The solution was filtered through a 0.45 μm syringe filter. The resulting solution was purified by RP HPLC. Lyophilization left a white solid (18 mg, 35%).

Workup

  1. temperatureThe solution was heated
  2. customExcess HCl was removed under a stream of N2 at 100° C
  3. customfor further drying
  4. dissolutiondissolved in 6 mL 1:1 CH3CN/H2O
  5. filtrationThe solution was filtered through a 0.45 μm syringe
  6. filtrationfilter
  7. customThe resulting solution was purified by RP HPLC
  8. waitLyophilization left a white solid (18 mg, 35%)

Sources & evidence

ORD record
ord-fb4eab4c590247d4a121735e6accb6c7
Source dataset
uspto-grants-2006_11
Patent number
US07132427B2

Reaction notes

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