Sodium Hydroxide → HCID 66881004, compound

HRID 1893523Notes

Reaction equation

HRID 1893523 reaction equation
[CH2:1]=[N:2][N:3]1[CH2:8][CH2:7][N:6]([S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N+:18]([O-:20])=[O:19])(=[O:11])=[O:10])[CH2:5][CH2:4]1.C([BH3-])#N.[Na+].[OH-].[Na+]>CO.C(O)(=O)C.O1CCCC1>[CH3:1][NH:2][N:3]1[CH2:8][CH2:7][N:6]([S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N+:18]([O-:20])=[O:19])(=[O:10])=[O:11])[CH2:5][CH2:4]1

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 66881481HCID 66881481, compound

Product 1

HCID 66881004HCID 66881004, compoundYield 56%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a methanol (50 ml)-tetrahydrofuran (30 ml) mixed solvent was added the compound (4.93 g, 16.53 mmol) obtained in step D, sodium cyanoborohydride (1.35 g, 21.49 mmol) was added under ice-cooling with stirring, and acetic acid (1 ml) and methanol (10 ml) solution were added dropwise by a small amount. After the completion of the dropwise addition, the mixture was further stirred at the same temperature for 30 min. The reaction mixture was poured into diluted aqueous sodium hydroxide solution, and the mixture was extracted with chloroform. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the solution was concentrated under reduced pressure. The obtained oil was purified by silica gel column chromatography (chloroform-methanol) to give the title compound (2.77 g, yield 56%) as a pale-yellow oil.

Workup

  1. additionwas added under ice-
  2. temperaturecooling
  3. additionAfter the completion of the dropwise addition
  4. stirringthe mixture was further stirred at the same temperature for 30 min
  5. extractionthe mixture was extracted with chloroform
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationThe insoluble material was filtered off
  9. concentrationthe solution was concentrated under reduced pressure
  10. customThe obtained oil was purified by silica gel column chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-377076c7176648af8ef4f03341123356
Source dataset
uspto-grants-2013_08
Patent number
US08513235B2

Reaction notes

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