Triphenylphosphine → HCID 59277723, compound

HRID 1097773Notes

Reaction equation

HRID 1097773 reaction equation
N(C(OCCCC)=O)=NC(OCCCC)=O.[CH3:17][O:18][C:19]([C:21]1[NH:22][CH:23]=[N:24][CH:25]=1)=[O:20].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O[CH:46]1[C:55]2[C:50](=[CH:51][CH:52]=[CH:53][CH:54]=2)[NH:49][C:48](=[O:56])[C:47]1([CH3:58])[CH3:57]>C1COCC1>[CH3:17][O:18][C:19]([C:21]1[N:22]=[CH:23][N:24]([CH:46]2[C:55]3[C:50](=[CH:51][CH:52]=[CH:53][CH:54]=3)[NH:49][C:48](=[O:56])[C:47]2([CH3:58])[CH3:57])[CH:25]=1)=[O:20]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 565661Methyl 4-imidazolecarboxylateHCID 3472400HCID 3472400, compoundHCID 592777124-Hydroxy-3,3-dimethyl-3,4-dihydro-1H-quinolin-2-one

Product 1

HCID 59277723HCID 59277723, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of di-butyl azodicarboxylate (145 mg, 0.6275 mmol) in 2 mL of dry THF is added dropwise to a suspension of 3H-Imidazole-4-carboxylic acid methyl ester (79 mg, 0.6275 mmol), PPh3 (165 mg, 0.6275 mmol), and 4-Hydroxy-3,3-dimethyl-3,4-dihydro-1H-quinolin-2-one (80 mg, 0.418 mg) in 3 mL of dry THF at 0° C. The resulting mixture is slowly warmed up to room temperature, and stirred for 2 h. The reaction is quenched with 2 M HCl and stirred for another 0.5 h. After concentration, the residue is dissolved in HCl (2 M) and extracted with ethyl acetate (20 mL×3). The aqueous layer is adjusted to pH 8-9 by addition of saturated NaHCO3 solution. Subsequently, the mixture is extracted with ethyl acetate (20 mL×3). The combined extracts are washed with brine, and dried over anhydrous Na2SO4. After concentration, the residue is purified by flash column first then by reverse phase HPLC and gives two title regioisomers.

Workup

  1. customThe reaction is quenched with 2 M HCl
  2. stirringstirred for another 0.5 h
  3. concentrationAfter concentration
  4. dissolutionthe residue is dissolved in HCl (2 M)
  5. extractionextracted with ethyl acetate (20 mL×3)
  6. additionThe aqueous layer is adjusted to pH 8-9 by addition of saturated NaHCO3 solution
  7. extractionSubsequently, the mixture is extracted with ethyl acetate (20 mL×3)
  8. washThe combined extracts are washed with brine
  9. dry with materialdried over anhydrous Na2SO4
  10. concentrationAfter concentration
  11. customthe residue is purified by flash column first
  12. customby reverse phase HPLC and gives two title regioisomers

Sources & evidence

ORD record
ord-81c8d230859d421d99759cf71235bd62
Source dataset
uspto-grants-2012_03
Patent number
US08143278B2

Reaction notes

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