Dimethylformamide → N-hydroxy-N-(1-hydroxy-2-naphthyl)-4-methoxycarbonyl-3-oxabutanamide

HRID 1886260노트

반응식

HRID 1886260 반응식
[C:1]([O:9][CH3:10])(=[O:8])[CH2:2][O:3][CH2:4][C:5]([O-:7])=O.CN(C=O)C.C(Cl)(=O)C(Cl)=O.Cl.[OH:23][C:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[CH:26][C:25]=1[NH:34][OH:35].C(N(CC)CC)C.OS([O-])(=O)=O.[K+]>C1COCC1.O.C(Cl)Cl>[OH:35][N:34]([C:25]1[CH:26]=[CH:27][C:28]2[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:24]=1[OH:23])[C:5](=[O:7])[CH2:4][O:3][CH2:2][C:1]([O:9][CH3:10])=[O:8]

참가 물질

10

반응물 6

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 516920Potassium bisulfateHCID 856138501-Hydroxy-2-naphthylhydroxylamine hydrochlorideHCID 86746156Methyl diglycolate

생성물 1

HCID 19877548N-hydroxy-N-(1-hydroxy-2-naphthyl)-4-methoxycarbonyl-3-oxabutanamide수율 69%

시약·촉매·용매 3

HCID 962Water용매HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

Into a 25 ml methylene chloride solution of 500 mg (3.38 mmol) of methyl diglycolate and 200 μl (3.38 mmol) of DMF was added 660 μl (7.60 mmol) of oxalyl chloride at 0° C., and the mixture was stirred as such for one hour. The mixture was added to a solution of 3.6 g (17 mmol) of 1-hydroxy-2-naphthylhydroxylamine hydrochloride, 3.5 ml (25 mmol) of triethylamine in THF (25 ml), and water (5 ml), at 0° C., and after stirring at 0° C. for one hour and at room temperature for one hour, the reaction was completed with aqueous KHSO4, and the mixture was extracted with methylene chloride. The organic layer was washed with 4N HCl and with saturated aqueous NaCl, and then dried over anhydrous magnesium sulfate, and after evaporation of the solvent under a reduced pressure, the residue was subjected to silica gel column chromatography to give 710 mg (69%) of the desired product.

후처리

  1. stirringafter stirring at 0° C. for one hour and at room temperature for one hour
  2. extractionthe mixture was extracted with methylene chloride
  3. washThe organic layer was washed with 4N HCl and with saturated aqueous NaCl
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customafter evaporation of the solvent under a reduced pressure

출처 및 근거

ORD 기록
ord-bf156d9c22174f4393ca26d80a946161
출처 데이터셋
uspto-grants-1992_09
특허 번호
US05149859

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