Acetic Acid → HCID 18972978, compound

HRID 2394309Notes

Reaction equation

HRID 2394309 reaction equation
C(O)(=O)C.[Cl:5][C:6]1[CH:7]=[C:8]([CH2:13][CH2:14][C:15](=O)[C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:9]=[CH:10][C:11]=1[Cl:12].[CH2:22]([NH2:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C([BH3-])#N.[Na+]>C(O)C>[CH2:22]([NH:29][CH:15]([CH2:14][CH2:13][C:8]1[CH:9]=[CH:10][C:11]([Cl:12])=[C:6]([Cl:5])[CH:7]=1)[C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7504BenzylamineHCID 5003444Sodium cyanoborohydrideHCID 18972968HCID 18972968, compound

Product 1

HCID 18972978HCID 18972978, compoundYield 33.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of acetic acid (0.29 ml, 5 mmol), the product of step (a) (700 mg, 2.5 mmol), benzylamine (0.56 ml, 5 mmol) and sodium cyanoborohydride (320 mg, 5 mmol) in ethanol (10 ml) was stirred at room temperature for 16 hours. The solvent was evaporated under reduced pressure and the residue was partitioned between ethyl acetate and aqueous sodium carbonate (saturated). The organic layer was dried (Na2SO4) and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with ethyl acetate/hexane (10:90) to give the title compound as an oil (310 mg). m/e (CI+) 366 (MH+).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was partitioned between ethyl acetate and aqueous sodium carbonate (saturated)
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel
  6. washeluting with ethyl acetate/hexane (10:90)

Sources & evidence

ORD record
ord-27703fa4876d41e4bb4d43713e538094
Source dataset
uspto-grants-1998_09
Patent number
US05811431

Reaction notes

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