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 864509Notes

Reaction equation

HRID 864509 reaction equation
[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]

Participants

5

Reactant 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

Product 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] benzothiazineYield 90.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-af7d66e069354d689d0f39a658dfc7e8
Source dataset
uspto-grants-1996_10
Patent number
US05563137

Reaction notes

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