Triethylamine → HCID 178493950, 화합물

HRID 1257991노트

반응식

HRID 1257991 반응식
[CH3:1][O:2][C:3]1[C:4]([CH3:16])=[C:5]([CH:9]=[CH:10][C:11]=1[S:12]([CH3:15])(=[O:14])=[O:13])[C:6]([OH:8])=O.Cl.[OH:18][C:19]1[N:23]([CH3:24])[N:22]=[CH:21][CH:20]=1.C1(N=C=NC2CCCCC2)CCCCC1.C(N(CC)CC)C>C(Cl)Cl>[CH3:1][O:2][C:3]1[C:4]([CH3:16])=[C:5]([C:6]([C:20]2[CH:21]=[N:22][N:23]([CH3:24])[C:19]=2[OH:18])=[O:8])[CH:9]=[CH:10][C:11]=1[S:12]([CH3:15])(=[O:14])=[O:13]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 142570143-Methoxy-2-methyl-4-(methylsulfonyl)benzoic acidHCID 178478934HCID 178478934, 화합물

생성물 1

HCID 178493950HCID 178493950, 화합물수율 25.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a stirred mixture of 3-methoxy-2-methyl-4-(methylsulfonyl)benzoic acid (340 mg, 1.39 mmol) and 5-hydroxy-1-methylpyrazole hydrochloride (230 mg) in anhydrous methylene chloride (10 mL) were added DCC (dicyclohexylcarbodiimide) (315 mg) and triethylamine (260 mg) at room temperature, followed by stirring for 2 hours. The reaction mixture was subjected to filtration through Celite, the filtrate was concentrated, and the obtained residue was dissolved in 10 mL of anhydrous acetonitrile. Triethylamine (260 mg) and acetone cyanohydrin in a catalytic amount were added thereto, and the reaction solution was stirred overnight at room temperature. 150 mL of ethyl acetate was added to the reaction mixture, and the solution was washed once with a 1N hydrochloric acid aqueous solution and washed once with a saturated brine. The organic layer was dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate:methanol=9:1) to obtain 5-hydroxy-1-methylpyrazol-4-yl 3-methoxy-2-methyl-4-(methylsulfonyl)phenyl ketone (115 mg).

후처리

  1. filtrationThe reaction mixture was subjected to filtration through Celite
  2. concentrationthe filtrate was concentrated
  3. dissolutionthe obtained residue was dissolved in 10 mL of anhydrous acetonitrile
  4. additionTriethylamine (260 mg) and acetone cyanohydrin in a catalytic amount were added
  5. stirringthe reaction solution was stirred overnight at room temperature
  6. addition150 mL of ethyl acetate was added to the reaction mixture
  7. washthe solution was washed once with a 1N hydrochloric acid aqueous solution
  8. washwashed once with a saturated brine
  9. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  10. distillationthe solvent was distilled off under reduced pressure
  11. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate:methanol=9:1)

출처 및 근거

ORD 기록
ord-a25749ab32a7424294c349729997c6f4
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08466088B2

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