HCID 86640029, compound → HCID 68663939, compound

HRID 452627Notes

Reaction equation

HRID 452627 reaction equation
C(OP([CH2:9][C:10]1[C:11]([NH:16][C:17](=O)[CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[N:12][CH:13]=[CH:14][CH:15]=1)(=O)OCC)C.C(O[K])(C)(C)C>C1(C)C=CC=CC=1.O1CCCC1>[C:20]1([CH2:19][CH2:18][C:17]2[NH:16][C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[CH:9]=2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 2

HCID 86640029HCID 86640029, compoundHCID 178418922HCID 178418922, compound

Product 1

HCID 68663939HCID 68663939, compoundYield 25.2%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of diethyl[[2-[(3-phenylpropionyl)amino]-3-pyridyl]methyl]phosphonate (13.56 g, 36.03 mmol) in toluene (150 mL) was added a suspension of tert-butoxy potassium (11.41 g, 86.47 mmol) in tetrahydrofuran (86.47 mL), and the resulting mixture was stirred at 90° C. for 1 hr. The reaction mixture was concentrated under reduced pressure, water was added to the residue, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1-0/1) and recrystallized from hexane/ethyl acetate to give the title compound (2.02 g, yield 25%) as colorless crystals.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, water
  2. additionwas added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1-0/1)
  8. customrecrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-cc63dac02e04494893d554ba35267628
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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