Sodium Hydroxide → HCID 178451370, compound

HRID 1682659Notes

Reaction equation

HRID 1682659 reaction equation
[C:1]([O:5][C:6]([CH2:8][O:9][C@H:10]1[CH2:15][CH2:14][C@H:13]([N:16]2CN(C)C(=O)N(C)C2)[CH2:12][CH2:11]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl-].[NH4+].[OH-].[Na+]>C(O)(C)(C)C>[NH2:16][C@H:13]1[CH2:14][CH2:15][C@H:10]([O:9][CH2:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:11][CH2:12]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 178481285HCID 178481285, compound

Product 1

HCID 178451370HCID 178451370, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

1H-NMR (CDCl3) δTMS : 4.20(s,4H), 3.98(s,2H), 3.49-3.23(m,1H), 2.84(s,6H), 2.88-2.75(m,1H), 2.18-2.06(m,2H), 2.06-1.93(m,2H), 1.47(s,9H), 1.44-1.16 (m,4H) trans-5-[4-[(t-Butoxycarbonyl)methyloxy]cyclohexyl]-1,3-dimethylhexahydro-2-oxo-1,3,5-triazine (300 mg, 0. 879 mmol) was dissolved in t-butanol (5 ml) and a saturated aqueous ammonium chloride solution (5 ml) was added, which was followed by refluxing under heating for 2 hours. The reaction mixture was adjusted to pH 10 with a 1N aqueous sodium hydroxide solution and extracted with benzene. The extract was washed with water and saturated brine, and dried over anhydrous sodium sulfate. After filtration, low boiling matters were distilled away from the filtrate under reduced pressure and the residue was purified by silica gel column chromatography (methylene chloride/methanol=10/1-5/1) to give 130 mg of t-butyl trans-(4-aminocyclohexyloxy)acetate as a colorless solid (57%).

Workup

  1. temperatureby refluxing
  2. temperatureunder heating for 2 hours
  3. extractionextracted with benzene
  4. washThe extract was washed with water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationAfter filtration, low boiling matters
  7. distillationwere distilled away from the filtrate under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (methylene chloride/methanol=10/1-5/1)

Sources & evidence

ORD record
ord-cac5ea0f5ab14fbd93e232049e2c7e20
Source dataset
uspto-grants-1997_06
Patent number
US05635527

Reaction notes

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