Potassium Carbonate → [4-Oxo-4-phenyl-3-(2-pyridinyl)butylidene]bisphosphonic acid tetraethyl ester hemihydrate

HRID 1450216Notes

Reaction equation

HRID 1450216 reaction equation
[CH2:1]([O:3][P:4]([C:9]([P:11](=[O:18])([O:15][CH2:16][CH3:17])[O:12][CH2:13][CH3:14])=[CH2:10])(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].COC1C=CC2N=[C:26]([NH:28][C:29](=O)[CH2:30][C:31](=[O:38])[C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)SC=2C=1.C(=O)([O-])[O-].[K+].[K+]>CO>[OH2:3].[CH2:16]([O:15][P:11]([CH:9]([P:4](=[O:8])([O:5][CH2:6][CH3:7])[O:3][CH2:1][CH3:2])[CH2:10][CH:30]([C:29]1[CH:31]=[CH:30][CH:29]=[CH:26][N:28]=1)[C:31](=[O:38])[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)(=[O:18])[O:12][CH2:13][CH3:14])[CH3:17].[O:38]=[C:31]([C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[CH:30]([C:29]1[CH:37]=[CH:32][CH:33]=[CH:26][N:28]=1)[CH2:10][CH:9]([P:4](=[O:8])([O:5][CH2:6][CH3:7])[O:3][CH2:1][CH3:2])[P:11](=[O:18])([O:12][CH2:13][CH3:14])[O:15][CH2:16][CH3:17]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11022954Tetraethyl vinylidene phosphonateHCID 19975336N-(6-methoxybenzothiazol-2-yl)-3-oxo-3-phenylpropanamide

Product 1

HCID 131718992[4-Oxo-4-phenyl-3-(2-pyridinyl)butylidene]bisphosphonic acid tetraethyl ester hemihydrate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethenylidenebisphosphonic acid tetraethyl ester (I, 3.00 g), 1-phenyl-2-(2-pyridinyl)ethanone (II, 2.17 g) and potassium carbonate (2.07 g) are stirred in methanol (20 ml) overnight. The reaction is concentrated under reduced pressure, taken up in ethyl acetate, washed with sodium chloride, dried with magnesium sulfate, and concentrated under reduced pressure. The product is chromatographed eluting with ethyl acetate. The appropriate fractions are pooled and concentrated to give the title compound, MS (m/e) 497, 452, 392, 302 and 288; IR (neat) 2983, 1683, 1597, 1580, 1470, 1448 and 1253 cm-1 ; NMR (CDCl3) 8.52, 8.02, 7.60, 7.49, 7.37, 7.11, 5.46, 4.12, 2.75, 2.55, 1.36, 1.25 and 1.16 δ.

Workup

  1. concentrationThe reaction is concentrated under reduced pressure
  2. washwashed with sodium chloride
  3. dry with materialdried with magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe product is chromatographed
  6. washeluting with ethyl acetate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-39d3bc82e4e4442c979df5ee72dedcf0
Source dataset
uspto-grants-1997_02
Patent number
US05602115

Reaction notes

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