Methyl chloroformate → HCID 86600904, compound

HRID 915007Notes

Reaction equation

HRID 915007 reaction equation
C(N(CC)CC)C.Cl.[NH2:9][CH:10]([C:19]1[CH:20]=[CH:21][C:22](=[O:28])[N:23]([CH:25]([CH3:27])[CH3:26])[N:24]=1)[C:11](=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.Cl[C:30]([O:32][CH3:33])=[O:31].CCCCCC>C(Cl)Cl.CCOC(C)=O>[CH:25]([N:23]1[C:22](=[O:28])[CH:21]=[CH:20][C:19]([CH:10]([NH:9][C:30](=[O:31])[O:32][CH3:33])[C:11](=[O:18])[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[N:24]1)([CH3:26])[CH3:27]

Participants

7

Reactant 4

HCID 6586Methyl chloroformateHCID 8058HexaneHCID 8471TriethylamineHCID 693314766-(1-amino-2-oxo-2-phenylethyl)-2-isopropyl-3(2H)-pyridazinone hydrochloride

Product 1

HCID 86600904HCID 86600904, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Under ice-cooling, a solution of triethylamine (16.8 ml) of CH2Cl2 (30 ml) was added dropwise to a suspension of 6-(1-amino-2-oxo-2-phenylethyl)-2-isopropyl-3(2H)-pyridazinone hydrochloride (15.42 g) and methyl chloroformate (4.65 ml) in CH2Cl2 (155 ml) and stirred at the same temperature for 30 minutes. The mixture was washed with water, 1N HCl and sat. aq. NaHCO3 solution, dried over MgSO4 and concentrated under reduced pressure to give a residue. The residue was subjected to column chromatography on silica gel eluting with a mixture of n-hexane and EtOAc (30:70 v/v) to give methyl [1-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-2-oxo-2-phenylethyl]carbamate as a syrup (15.78 g), which was identical to the authentic sample (the product of Preparation 5) by IR, MS and NMR spectra.

Workup

  1. temperatureUnder ice-cooling
  2. washThe mixture was washed with water, 1N HCl and sat. aq. NaHCO3 solution
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customto give a residue

Sources & evidence

ORD record
ord-9cb4b9707be846f6b75657fde278aea4
Source dataset
uspto-grants-2007_09
Patent number
US07265120B2

Reaction notes

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