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

HRID 1787801ノート

反応式

HRID 1787801 の反応式
[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

参加物

7

反応物 4

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

生成物 1

HCID 569517Methyl 4-(2-benzoylhydrazino)-4-oxobutanoate収率 32.7%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3805461a52d641f885f11aa035677179
出典データセット
uspto-grants-2009_03
特許番号
US07511050B2

反応ノート

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