Acetic Acid → HCID 59540450, compound

HRID 923386Notes

Reaction equation

HRID 923386 reaction equation
[N+:1]([C:4]1[CH:21]=[CH:20][C:7]([CH2:8][NH:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:22][C:23]([CH3:25])=O.C(O)(=O)C.C([BH3-])#N.[Na+]>CO.C(Cl)Cl>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)[CH:23]([CH3:25])[CH3:22])=[CH:20][CH:21]=1)([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 180AcetoneHCID 4558515HCID 4558515, compoundHCID 5003444Sodium cyanoborohydride

Product 1

HCID 59540450HCID 59540450, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of bis(4-nitrobenzyl)amine (50 mg, 0.174 mmol) and acetone (51.1 μL, 0.696 mmol) in methanol (752 μL)/acetic acid (39.6 μL)/CH2Cl2 (79 μL) was stirred at room temperature for 1 hour. The reaction was cooled to 0° C. and sodium cyanoborohydride (32.8 mg, 0.522 mmol) was added. The mixture was stirred at 0° C. for 1 hour, and allowed to warm to rt and stirred overnight. The reaction was concentrated and the residue was partitioned between EtOAc and saturated aqueous NaHCO3. The organic layer was washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. Purification by flash chromatography (silica gel, 50% EtOAc/hexane) afforded the title product (42.8 mg, 75%). MS (ESI) m/z 329.9 (M+H)+.

Workup

  1. temperatureThe reaction was cooled to 0° C.
  2. stirringThe mixture was stirred at 0° C. for 1 hour
  3. temperatureto warm to rt
  4. stirringstirred overnight
  5. concentrationThe reaction was concentrated
  6. customthe residue was partitioned between EtOAc and saturated aqueous NaHCO3
  7. washThe organic layer was washed with brine
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customPurification by flash chromatography (silica gel, 50% EtOAc/hexane)

Sources & evidence

ORD record
ord-16ce5469529f4bccb8332644c2536d54
Source dataset
uspto-grants-2016_03
Patent number
US09278922B2

Reaction notes

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