Dimethylformamide → HCID 23077490, 화합물

HRID 1349457노트

반응식

HRID 1349457 반응식
[CH2:1]([O:8][C:9]1[C:14](=[O:15])[CH:13]=[CH:12][O:11][C:10]=1[C:16]([OH:18])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:19]([Cl:24])(=O)[C:20]([Cl:22])=O.C[N:26]([CH3:29])C=O>C(Cl)(Cl)Cl>[Cl:22][C:20]1[CH:1]=[C:2]([CH:3]=[CH:4][C:19]=1[Cl:24])[CH2:29][NH:26][C:16]([C:10]1[O:11][CH:12]=[CH:13][C:14](=[O:15])[C:9]=1[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:18]

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 217925463-(Benzyloxy)-4-oxo-4h-pyran-2-carboxylic acid

생성물 1

HCID 23077490HCID 23077490, 화합물

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

To a solution of 3-benzyloxy-4-oxo-4H-pyran-2-carboxylic acid (0.4 g) prepared according to the method described in references (JP-A-2-502281 (WO88/06588), J. Med. Chem., 1999, 42, 4814–4823) in chloroform (30 ml) were added oxalyl chloride (0.21 ml) and dimethylformamide (0.01 ml), and the mixture was stirred at room temperature for 30 min. The reaction solvent was evaporated under reduced pressure, toluene was added, the mixture was concentrated and dissolved in chloroform (5 ml). 3,4-Dichlorobenzylamine (0.23 ml) and triethylamine (0.34 ml) were added successively under ice-cooling, and the mixture was stirred under ice-cooling for 20 min. 5% Aqueous potassium hydrogen sulfate solution was added to the obtained reaction mixture and the mixture was extracted with. chloroform. The organic layer was washed with saturated brine and dried over sodium sulfate. The solvent was evaporated and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1–1:8) to give N-(3,4-dichlorobenzyl)-3-benzyloxy-4-oxo-4H-pyran-2-carboxamide (0.43 g).

후처리

  1. customThe reaction solvent was evaporated under reduced pressure, toluene
  2. additionwas added
  3. concentrationthe mixture was concentrated
  4. dissolutiondissolved in chloroform (5 ml)
  5. addition3,4-Dichlorobenzylamine (0.23 ml) and triethylamine (0.34 ml) were added successively under ice-
  6. temperaturecooling
  7. stirringthe mixture was stirred under ice-
  8. temperaturecooling for 20 min
  9. addition5% Aqueous potassium hydrogen sulfate solution was added to the obtained reaction mixture
  10. extractionthe mixture was extracted with
  11. washThe organic layer was washed with saturated brine
  12. dry with materialdried over sodium sulfate
  13. customThe solvent was evaporated
  14. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1–1:8)

출처 및 근거

ORD 기록
ord-2ad07f7763fc42ddbab4648a593c52ec
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07211572B2

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