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

HRID 1886262ノート

反応式

HRID 1886262 の反応式
[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]

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-712c8552569643b0afb458dd08cea1fc
出典データセット
uspto-grants-1992_09
特許番号
US05149859

反応ノート

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