Acetic Acid → 3-(2-Tert-butoxycarbonyl-2-methylhydrazino)methylene-6-chloro-4-oxo-1-propionyl-1,2,3,4-tetrahydroquinoline

HRID 653133ノート

反応式

HRID 653133 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12](=[O:15])[CH2:13][CH3:14])[CH2:7][C:6](=[CH:16][N:17](C)C)[C:5]2=[O:20].[C:21]([O:25][C:26]([N:28]([CH3:30])N)=[O:27])([CH3:24])([CH3:23])[CH3:22].C(O)(=O)C>CO.O1CCCC1>[C:21]([O:25][C:26]([N:28]([CH3:30])[NH:17][CH:16]=[C:6]1[C:5](=[O:20])[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([Cl:1])[CH:3]=2)[N:8]([C:12](=[O:15])[CH2:13][CH3:14])[CH2:7]1)=[O:27])([CH3:24])([CH3:23])[CH3:22]

参加物

6

反応物 3

HCID 176Acetic AcidHCID 37482801-Boc-1-methylhydrazine2 回HCID 54453990HCID 54453990、化合物

生成物 1

HCID 540949343-(2-Tert-butoxycarbonyl-2-methylhydrazino)methylene-6-chloro-4-oxo-1-propionyl-1,2,3,4-tetrahydroquinoline収率 78%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 6-chloro-3-dimethylaminomethylene-4-oxo-1-propionyl-1,2,3,4-tetrahydroquinoline (2.00 g), 1-tert-butoxycarbonyl-1-methylhydrazine (1.50 g) and acetic acid (1.20 ml) in methanol (100 ml) and tetrahydrofuran (100 ml) was refluxed for 9 hours with stirring. 1-tert-Butoxycarbonyl-1-methylhydrazine (1.50 g) was added to the mixture and the stirring was continued for 8 hours at reflux conditions. After the solvent was evaporated in vacuo, saturated aqueous sodium hydrogen carbonate (15 ml) was added to the mixture and extracted with ethyl acetate (30 ml). The extract was washed with water, dried over magnesium sulfate and evaporated in vacuo. The residue (3.90 g) was chromatographed on silica gel by eluting with chloroform to give 3-(2-tert-butoxycarbonyl-2-methylhydrazino)methylene-6-chloro-4-oxo-1-propionyl-1,2,3,4-tetrahydroquinoline (2.10 g) as yellow amorphous.

後処理

  1. temperatureat reflux conditions
  2. customAfter the solvent was evaporated in vacuo, saturated aqueous sodium hydrogen carbonate (15 ml)
  3. additionwas added to the mixture
  4. extractionextracted with ethyl acetate (30 ml)
  5. washThe extract was washed with water
  6. dry with materialdried over magnesium sulfate
  7. customevaporated in vacuo
  8. customThe residue (3.90 g) was chromatographed on silica gel
  9. washby eluting with chloroform

出典と根拠

ORDレコード
ord-3d9e037032af4741b155466954806f96
出典データセット
uspto-grants-1987_06
特許番号
US04675324

反応ノート

読み込み中…