Di-tert-butyl dicarbonate → Ethyl 3-(3-isocyanato-4-methoxyphenyl)-2-isopropoxypropanoate

HRID 1985411Notes

Reaction equation

HRID 1985411 reaction equation
[C:1](OC(OC(C)(C)C)=O)(OC(C)(C)C)=[O:2].[NH2:16][C:17]1[CH:18]=[C:19]([CH2:25][CH:26]([O:32][CH:33]([CH3:35])[CH3:34])[C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH:20]=[CH:21][C:22]=1[O:23][CH3:24].S(=O)(=O)(O)O.C(#N)C>C(#N)C.CN(C)C1C=CN=CC=1>[N:16]([C:17]1[CH:18]=[C:19]([CH2:25][CH:26]([O:32][CH:33]([CH3:34])[CH3:35])[C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH:20]=[CH:21][C:22]=1[O:23][CH3:24])=[C:1]=[O:2]

Participants

6

Reactant 3

HCID 90495Di-tert-butyl dicarbonateHCID 22284053Sulfuric acid acetonitrileHCID 22494286Ethyl 3-(3-amino-4-methoxyphenyl)-2-isopropoxypropanoate

Product 1

HCID 22927009Ethyl 3-(3-isocyanato-4-methoxyphenyl)-2-isopropoxypropanoateYield 21.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent2×

Procedure

0.13 g of di-t-Butyl dicarbonate was dissolved in 2.5 ml of acetonitrile, and a solution containing 60 mg of 4-dimethylaminopyridine and 0.12 g of ethyl 3-(3-amino-4-methoxy-phenyl)-2-isopropoxypropanoate in acetonitrile were added thereto, and the mixture was stirred at room temperature for 10 minutes. The reaction solution was cooled in ice, and 0.73 ml of 40% sulfuric acid-acetonitrile solution was added and stirring was continued at room temperature for 2 minutes, then the mixture was extracted with hexane. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated, to give 28 mg of the title compound.

Workup

  1. additionwere added
  2. temperatureThe reaction solution was cooled in ice
  3. stirringstirring
  4. waitwas continued at room temperature for 2 minutes
  5. extractionthe mixture was extracted with hexane
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was evaporated

Sources & evidence

ORD record
ord-842be2a921ee493d9c436fe1e01b24a0
Source dataset
uspto-grants-2009_06
Patent number
US07544835B2

Reaction notes

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