Sodium Azide → (2R, 3R, 4S, 4aS, 10aR)-2-azidomethyl-8-chloro-3, 4-diacetoxy-10-(2-diethylaminoethyl)-2, 3, 4, 4a, 10, 10a-hexahydropyrano [3, 2-b] [1, 4] benzothiazine

HRID 864509노트

반응식

HRID 864509 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:10][C@H:9]3[C@@H:11]([O:30][C:31](=[O:33])[CH3:32])[C@@H:12]([O:26][C:27](=[O:29])[CH3:28])[C@@H:13](OS(C4C=CC(C)=CC=4)(=O)=O)[O:14][C@H:8]3[N:7]([CH2:34][CH2:35][N:36]([CH2:39][CH3:40])[CH2:37][CH3:38])[C:6]=2[CH:41]=1.[N-:42]=[N+:43]=[N-:44].[Na+].[CH:46](Cl)(Cl)Cl.CC(C)=O>CS(C)=O>[N:42]([CH2:46][C@H:13]1[O:14][C@@H:8]2[C@@H:9]([S:10][C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:41][C:6]=3[N:7]2[CH2:34][CH2:35][N:36]([CH2:37][CH3:38])[CH2:39][CH3:40])[C@@H:11]([O:30][C:31](=[O:33])[CH3:32])[C@@H:12]1[O:26][C:27](=[O:29])[CH3:28])=[N+:43]=[N-:44]

참가 물질

5

반응물 3

HCID 33557Sodium AzideHCID 15930782Chloroform acetoneHCID 86749916(2R, 3R, 4S, 4aS, 10aR)-8-chloro-3, 4-diacetoxy-10-(2-diethylaminoethyl)-2-(4-methylphenylsulfonyloxy)-2, 3, 4, 4a, 10, 10a-hexahydropyrano [3, 2-b] [1, 4] benzothiazine

생성물 1

HCID 86749915(2R, 3R, 4S, 4aS, 10aR)-2-azidomethyl-8-chloro-3, 4-diacetoxy-10-(2-diethylaminoethyl)-2, 3, 4, 4a, 10, 10a-hexahydropyrano [3, 2-b] [1, 4] benzothiazine수율 90.2%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

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온도
100 °C

실험 절차

To the solution of 14.0 g of the compound (36) obtained in Example 35 in 140 ml of dimethylsulfoxide, 14.0 g of sodium azide was added, and the mixture was heated with stirring for 45 minutes at 100 ° C. The reaction solution was poured into ice water, the mixture was extracted with ethyl acetate, and the organic layer was washed with saturated aqueous sodium chloride. The solution was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain 10.1 g (yield 90.2%) of the title compound from the fraction of chloroform-acetone (1:1).

후처리

  1. temperaturethe mixture was heated
  2. extractionthe mixture was extracted with ethyl acetate
  3. washthe organic layer was washed with saturated aqueous sodium chloride
  4. dry with materialThe solution was dried over anhydrous magnesium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-af7d66e069354d689d0f39a658dfc7e8
출처 데이터셋
uspto-grants-1996_10
특허 번호
US05563137

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