Acetic Anhydride → HCID 68283126, compound

HRID 541493Notes

Reaction equation

HRID 541493 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[CH:5]([CH2:14][CH2:15][N:16]2C(=O)C3[C:18](=CC=CC=3)[C:17]2=[O:26])[CH2:4][CH:3]=1.[BH4-].[Na+].[OH-].[Na+].CN(C1C=CC=CN=1)C.C(OC(=O)C)(=O)C>C(O)(C)C.O.ClCCl.Cl.CC(C)=O>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[CH:5]([CH2:14][CH2:15][NH:16][C:17](=[O:26])[CH3:18])[CH2:4][CH:3]=1

Participants

11

Reactant 5

HCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 218852-DimethylaminopyridineHCID 4311764Sodium borohydrideHCID 68284298HCID 68284298, compound

Product 1

HCID 68283126HCID 68283126, compoundYield 64%

Reagents, catalysts & solvents 5

HCID 313Hydrochloric AcidCatalystHCID 180AcetoneSolventHCID 962WaterSolvent2×HCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of the compound obtained in Step B (390 mg, 0.95 mmol) in isopropanol (10 mL) at ambient temperature there is added sodium borohydride (179 mg, 4.7 mmol). The mixture is stirred for 3 hours under reflux, and then a solution of sodium hydroxide (76 mg, 1.9 mmol) in water (2.0 mL) is added dropwise. The mixture is maintained under reflux for 30 minutes, and then acetone (1.5 mL) is added. After 10 minutes, the mixture is cooled to ambient temperature before being concentrated under reduced pressure. The oil thereby obtained is dissolved in dichloromethane (10 mL). Dimethylaminopyridine (255 mg, 2.1 mmol) is then added, followed by acetic anhydride (200 μL, 2.1 mmol) dropwise. The solution is stirred at ambient temperature for 1 hour and then water is added. A few drops of hydrochloric acid (1N) are also added to obtain an acid pH. The aqueous phase is extracted with dichloromethane and the organic phases are washed with saturated NaCl solution, dried over magnesium sulphate, filtered and evaporated. The title compound is obtained after purification by flash column chromatography (ethyl acetate-petroleum ether: 90-10, then ethyl acetate-methanol: 90-10) in the form of an oil in a yield of 64%.

Workup

  1. temperatureunder reflux
  2. temperatureThe mixture is maintained
  3. temperatureunder reflux for 30 minutes
  4. waitAfter 10 minutes
  5. concentrationbefore being concentrated under reduced pressure
  6. customThe oil thereby obtained
  7. stirringThe solution is stirred at ambient temperature for 1 hour
  8. customto obtain an acid pH
  9. extractionThe aqueous phase is extracted with dichloromethane
  10. washthe organic phases are washed with saturated NaCl solution
  11. dry with materialdried over magnesium sulphate
  12. filtrationfiltered
  13. customevaporated

Sources & evidence

ORD record
ord-1332e35a32954348891b3ce4fce99192
Source dataset
uspto-grants-2014_10
Patent number
US08871975B2

Reaction notes

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