Benzoylhydrazine → Methyl 4-(2-benzoylhydrazino)-4-oxobutanoate

HRID 1787801Notes

Reaction equation

HRID 1787801 reaction equation
[C:1]([NH:9][NH2:10])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:11]([O:18][CH3:19])(=[O:17])[CH2:12][CH2:13][C:14]([O-])=[O:15].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C)C1C=CN=CC=1.CN(C=O)C>[C:1]([NH:9][NH:10][C:14](=[O:15])[CH2:13][CH2:12][C:11]([O:18][CH3:19])=[O:17])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 11955BenzoylhydrazineHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 6930703Mono-Methyl Succinate

Product 1

HCID 569517Methyl 4-(2-benzoylhydrazino)-4-oxobutanoateYield 32.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

The mixture of benzhydrazide (1.5 g, 11.0 mmol), butanedioic acid, monomethyl ester (2.0 g, 15 mmol), benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (5.4 g, 12 mmol), N,N-diisopropylethylamine (3.8 mL, 22 mmol) and 4-dimethylaminopyridine (0.87 g, 7.2 mmol) in DMF (30 mL) was stirred at room temperature overnight. The mixture was quenched with water and extracted with ethyl acetate three times. The combined organic layers were washed by brine, dried over sodium sulfate, filtered and concentrated. The crude residue was purified by flash column chromatography to yield the desired product (900 mg, 32.6%). LCMS calculated for C12H15N2O4(M+H): 251.1; found: 251.1.

Workup

  1. customThe mixture was quenched with water
  2. extractionextracted with ethyl acetate three times
  3. washThe combined organic layers were washed by brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-3805461a52d641f885f11aa035677179
Source dataset
uspto-grants-2009_03
Patent number
US07511050B2

Reaction notes

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