Triethylamine → N-hydroxy-N-(1-methoxy-2-naphthylmethyl)-4-methoxycarbonylbutanamide

HRID 1886262

반응식

HRID 1886262 반응식
[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[CH2:13][NH:14][OH:15].C(N(CC)CC)C.[CH3:23][O:24][C:25]([CH2:27][CH2:28][CH2:29][C:30](O)=[O:31])=[O:26].S([O-])(O)(=O)=O.[K+]>C1COCC1.O.C(OCC)(=O)C.CCCCCC>[OH:15][N:14]([CH2:13][C:4]1[CH:5]=[CH:6][C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[O:2][CH3:1])[C:30](=[O:31])[CH2:29][CH2:28][CH2:27][C:25]([O:24][CH3:23])=[O:26]

참가 물질

9

반응물 4

HCID 8471TriethylamineHCID 73917Monomethyl glutarateHCID 516920Potassium bisulfateHCID 544655221-Methoxy-2-naphthylmethylhydroxylamine

생성물 1

HCID 54304225N-hydroxy-N-(1-methoxy-2-naphthylmethyl)-4-methoxycarbonylbutanamide수율 64%

시약·촉매·용매 4

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매HCID 8857Ethyl Acetate용매

반응 조건

온도
0 °C

실험 절차

Into a solution of 267 mg (1.33 mmol) of 1-methoxy-2-naphthylmethylhydroxylamine and 185 μl (1.33 mmol) of triethylamine in THF (15 ml) and water (3 ml) was added under 0° C. a solution of 219 mg (1.33 mmol) of acid chloride of 4-methoxycarbonylbutanoic acid in THF (3 ml), followed by stirring at 0° C. for one hour and at room temperature for one hour. After the reaction, an aqueous potassium hydrogen sulfate was added, and the mixture extracted with methylene chloride. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under a reduced pressure. The crude product obtained was subjected to silica gel column chromatography (hexane: ethyl acetate=1:1) to give 279 mg (64%) of the desired product.

후처리

  1. customAfter the reaction
  2. extractionthe mixture extracted with methylene chloride
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under a reduced pressure
  5. customThe crude product obtained

출처 및 근거

ORD 기록
ord-712c8552569643b0afb458dd08cea1fc
출처 데이터셋
uspto-grants-1992_09
특허 번호
US05149859

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