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

HRID 36164

Reaction equation

HRID 36164 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-11b6ca9ebeb54b8eaeeb3093531cc74c
Source dataset
uspto-grants-1995_05
Patent number
US05412141

Linked notes

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