Sodium sulfate decahydrate → HCID 23155447, compound

HRID 2080748Notes

Reaction equation

HRID 2080748 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9]([C:11]1[CH:31]=[CH:30][C:14]2[N:15]=[C:16]([CH2:19][CH2:20][CH2:21][CH2:22][N:23]([CH2:27][CH2:28][CH3:29])[CH2:24][CH2:25][CH3:26])[N:17]([CH3:18])[C:13]=2[CH:12]=1)=O.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[CH2:27]([N:23]([CH2:24][CH2:25][CH3:26])[CH2:22][CH2:21][CH2:20][CH2:19][C:16]1[N:17]([CH3:18])[C:13]2[CH:12]=[C:11]([CH2:9][OH:8])[CH:31]=[CH:30][C:14]=2[N:15]=1)[CH2:28][CH3:29]

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydrideHCID 67103508HCID 67103508, compound

Product 1

HCID 23155447HCID 23155447, compoundYield 87.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Lithium aluminum hydride (120 mg) was suspended in THF (3.0 ml) and then cooled to 0° C. After that, a solution of the compound (305 mg) obtained in Example 13-3 in THF (4.5 ml) was dropped in the suspension. The whole was warmed back to room temperature and stirred for 2 hours. After completion of the reaction, sodium sulfate decahydrate was gradually added to the solution until bubbling was stopped, and a 1 mol/l sodium hydroxide aqueous solution was then added to the mixture until a white precipitate was generated. Solid matter was separated by filtration and the solvent was then distilled off from the filtrate under reduced pressure. The residue was purified through silica gel column chromatography (chloroform/ethyl acetate), thereby obtaining the subject compound (246 mg) as a brown oily substance.

Workup

  1. temperatureThe whole was warmed back to room temperature
  2. additionwas gradually added to the solution
  3. customuntil bubbling
  4. additiona 1 mol/l sodium hydroxide aqueous solution was then added to the mixture until a white precipitate
  5. customSolid matter was separated by filtration
  6. distillationthe solvent was then distilled off from the filtrate under reduced pressure
  7. customThe residue was purified through silica gel column chromatography (chloroform/ethyl acetate)

Sources & evidence

ORD record
ord-961640551cb64717af21f6b946ea1f04
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

Loading…