Phosphorus oxychloride → HCID 59715638, compound

HRID 604789Notes

Reaction equation

HRID 604789 reaction equation
P(Cl)(Cl)(Cl)=O.O[CH:7]([C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH3:30])[CH:24]=1)[CH2:8][NH:9][C:10](=O)[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][CH2:20][CH3:21])=[CH:14][CH:13]=1.C(=O)([O-])O.[Na+]>C(#N)C>[CH2:18]([C:15]1[CH:16]=[CH:17][C:12]([CH2:11][C:10]2[C:28]3[C:23](=[CH:24][C:25]([O:29][CH3:30])=[CH:26][CH:27]=3)[CH:7]=[CH:8][N:9]=2)=[CH:13][CH:14]=1)[CH2:19][CH2:20][CH3:21]

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 59715623HCID 59715623, compound

Product 1

HCID 59715638HCID 59715638, compoundYield 15.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Phosphorus oxychloride (1.6 ml) was added to a solution of the compound of Example B145 (600 mg, 1.7 mmol) in acetonitrile (15 ml), and the mixture was stirred under reflux for 1 hour 30 minutes. The mixture was cooled on ice, made alkaline with a 5% aqueous sodium hydrogencarbonate solution, extracted with ethyl acetate, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (82 mg).

Workup

  1. temperatureunder reflux for 1 hour 30 minutes
  2. temperatureThe mixture was cooled on ice
  3. extractionextracted with ethyl acetate
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-db38cc879d8241fe84cfc0ac4251d041
Source dataset
uspto-grants-2011_03
Patent number
US07910712B2

Reaction notes

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