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

HRID 653133노트

반응식

HRID 653133 반응식
[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]

참가 물질

6

반응물 3

HCID 176Acetic AcidHCID 37482801-Boc-1-methylhydrazine2회HCID 54453990HCID 54453990, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3d9e037032af4741b155466954806f96
출처 데이터셋
uspto-grants-1987_06
특허 번호
US04675324

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