Ethyl Acetate → Benzyl [4-(3-methoxypyridin-4-yl)-2-(propan-2-yloxy)phenyl]carbamate

HRID 518803Notes

Reaction equation

HRID 518803 reaction equation
C(=O)(O)[O-].[Na+].Cl[C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8].[CH3:17][O:18][C:19]1[CH:20]=[N:21][CH:22]=[CH:23][C:24]=1[C:25]1[CH:31]=[CH:30][C:28]([NH2:29])=[C:27]([O:32][CH:33]([CH3:35])[CH3:34])[CH:26]=1.C(OCC)(=O)C>C1COCC1.O>[CH3:17][O:18][C:19]1[CH:20]=[N:21][CH:22]=[CH:23][C:24]=1[C:25]1[CH:31]=[CH:30][C:28]([NH:29][C:7](=[O:8])[O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:27]([O:32][CH:33]([CH3:35])[CH3:34])[CH:26]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 10387Benzyl chloroformate3×HCID 516892Sodium BicarbonateHCID 866979734-(3-Methoxypyridin-4-yl)-2-(propan-2-yloxy)aniline

Product 1

HCID 86697974Benzyl [4-(3-methoxypyridin-4-yl)-2-(propan-2-yloxy)phenyl]carbamate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

85 ml of a saturated aqueous sodium bicarbonate solution and then 3.81 ml of benzyl chloroformate are added to a solution of 4.6 g of 4-(3-methoxypyridin-4-yl)-2-(propan-2-yloxy)aniline in 115 ml of THF. The reaction medium is stirred overnight at ambient temperature and then 3.81 ml of benzyl chloroformate are added and the reaction medium is stirred at ambient temperature for 2 hours. 2.54 ml of benzyl chloroformate are added and the reaction medium is stirred for a further 2 hours at ambient temperature. The reaction medium is poured into 100 ml of ethyl acetate and 50 ml of water. The two phases are separated and the aqueous phase is extracted with twice 50 ml of ethyl acetate. The combined organic phases are dried over magnesium sulfate, filtered and evaporated under reduced pressure. The residue is purified on 100 g of silica, elution being carried out with dichloromethane/acetone (100/0 to 95/5), so as to give 3.12 g of benzyl [4-(3-methoxypyridin-4-yl)-2-(propan-2-yloxy)phenyl]carbamate in the form of a colourless oil.

Workup

  1. stirringthe reaction medium is stirred at ambient temperature for 2 hours
  2. stirringthe reaction medium is stirred for a further 2 hours at ambient temperature
  3. customThe two phases are separated
  4. extractionthe aqueous phase is extracted with twice 50 ml of ethyl acetate
  5. dry with materialThe combined organic phases are dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe residue is purified on 100 g of silica, elution

Sources & evidence

ORD record
ord-2e1f71fc66ca4b08a65e214b807fdd70
Source dataset
uspto-grants-2015_08
Patent number
US09115140B2

Reaction notes

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