Water → HCID 59494747, compound

HRID 872024Notes

Reaction equation

HRID 872024 reaction equation
N1C=CC=CC=1.Cl[C:8]([O:10][CH3:11])=[O:9].[NH2:12][CH2:13][CH2:14][O:15][C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[C:18]([CH2:26][N:27]([CH:35]2[CH2:37][CH2:36]2)[C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[CH:17]=1.O>C(Cl)(Cl)Cl>[C:30]([O:29][C:28]([N:27]([CH2:26][C:18]1[CH:17]=[C:16]([O:15][CH2:14][CH2:13][NH:12][C:8](=[O:9])[O:10][CH3:11])[C:25]2[C:20]([CH:19]=1)=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:35]1[CH2:36][CH2:37]1)=[O:34])([CH3:31])([CH3:32])[CH3:33]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 6586Methyl chloroformateHCID 68520113HCID 68520113, compound

Product 1

HCID 59494747HCID 59494747, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Pyridine (272 μL) and methyl chloroformate (130 μL) were added to a solution of tert-butyl {[4-(2-aminoethoxy)-2-naphthyl]methyl}cyclopropylcarbamate (400 mg) in chloroform (4.0 ml) under ice-cooling and the mixture was stirred at room temperature for an hour. Water was added to the reaction mixture and it was extracted with chloroform. The organic layer was washed with a saturated aqueous solution of sodium bicarbonate and saturated brine successively, dried over sodium sulfate and concentrated in vacuo. The resulted residue was purified with NH-silica gel column chromatography (eluting solvent: n-hexane to n-hexane/ethyl acetate=2/1) to give methyl {2-[(3-{[(tert-butoxycarbonyl)(cyclopropyl)amino]methyl}-1-naphthyl)oxy]ethyl}carbamate (418 mg) as a colorless oil.

Workup

  1. temperaturecooling
  2. extractionwas extracted with chloroform
  3. washThe organic layer was washed with a saturated aqueous solution of sodium bicarbonate and saturated brine successively
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe resulted residue was purified with NH-silica gel column chromatography (eluting solvent: n-hexane to n-hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-ae15d97320224d6d9febfd9e512185c9
Source dataset
uspto-grants-2015_03
Patent number
US08975252B2

Reaction notes

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