Water → HCID 70258861, compound

HRID 1842076Notes

Reaction equation

HRID 1842076 reaction equation
S(S([O-])=O)([O-])=O.[Na+].[Na+].[N+:9]([C:12]1[CH:13]=[C:14]([C@:18]23[CH2:27][CH2:26][CH2:25][CH2:24][C@H:23]2[CH2:22][S:21][C:20]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[N:19]3)[CH:15]=[CH:16][CH:17]=1)([O-])=O.O>C(O)C>[C:31]([O:30][C:29](=[O:35])[NH:28][C:20]1[S:21][CH2:22][C@@H:23]2[CH2:24][CH2:25][CH2:26][CH2:27][C@:18]2([C:14]2[CH:15]=[CH:16][CH:17]=[C:12]([NH2:9])[CH:13]=2)[N:19]=1)([CH3:34])([CH3:32])[CH3:33]

Participants

5

Reactant 3

HCID 962WaterHCID 24489Sodium DithioniteHCID 70827630HCID 70827630, compound

Product 1

HCID 70258861HCID 70258861, compoundYield 30.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A saturated solution of sodium dithionite (879 mg) was added to a solution of tert-butyl(−)-[(4aR*,8aS*)-8a-(3-nitrophenyl)-4a,5,6,7,8,8a-hexahydro-4H-benzo[d][1,3]thiazin-2-yl]carbamate (395 mg) in ethanol (20 mL) at room temperature. After stirring at room temperature for 10 minutes, ethanol (10 mL) was further added to the reaction solution. After stirring at room temperature for five minutes, water (10 mL) was further added. The reaction solution was warmed to 40° C. and stirred for 30 minutes. After confirming completion of the reaction, the reaction solution was cooled to room temperature. The excess of ethanol in the reaction solution was evaporated under reduced pressure and then the aqueous layer was extracted with ethyl acetate. The organic layer was washed with a saturated sodium chloride solution and dried over anhydrous magnesium sulfate. The drying agent was removed by filtration and then the filtrate was concentrated under reduced pressure. The residue was purified by NH-silica gel column chromatography to obtain the title compound (110 mg).

Workup

  1. stirringAfter stirring at room temperature for five minutes
  2. temperatureThe reaction solution was warmed to 40° C.
  3. stirringstirred for 30 minutes
  4. customcompletion of the reaction
  5. temperaturethe reaction solution was cooled to room temperature
  6. customThe excess of ethanol in the reaction solution was evaporated under reduced pressure
  7. extractionthe aqueous layer was extracted with ethyl acetate
  8. washThe organic layer was washed with a saturated sodium chloride solution
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customThe drying agent was removed by filtration
  11. concentrationthe filtrate was concentrated under reduced pressure
  12. customThe residue was purified by NH-silica gel column chromatography

Sources & evidence

ORD record
ord-0498a9ca665f465a831c4e8095461777
Source dataset
uspto-grants-2015_02
Patent number
US08946211B2

Reaction notes

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