Ethyl Acetate → HCID 12800846, compound

HRID 866479Notes

Reaction equation

HRID 866479 reaction equation
Br.[NH2:2][CH2:3][C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1)=[O:5].CCOC(C)=O.C([O-])([O-])=O.[K+].[K+]>O>[NH2:2][CH2:3][C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1)=[O:5]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 20516785p-Nitrobenzyl glycinate hydrobromide

Product 1

HCID 12800846HCID 12800846, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

p-Nitrobenzyl glycinate hydrobromide (2.91 g., 10mMol) is suspended in H2O (5 ml.) and layered with EtOAc (15 ml.) The mixture is cooled in ice and stirred while ice-cold, saturated aqueous K2CO3 (2.5 ml.) is added. The layers are separated and the aqueous portion is extracted with more EtOAc (3 × 5 ml.). The combined EtOAc solution is washed with H2O and brine, dried with Na2SO4, filtered, and evaporated in vacuo to an off-white solid (1.81 g.). Recrystallization from Et2O yields p-nitrobenzyl glycinate as small, off-white needles.

Workup

  1. temperatureis cooled in ice
  2. additionis added
  3. customThe layers are separated
  4. extractionthe aqueous portion is extracted with more EtOAc (3 × 5 ml.)
  5. washThe combined EtOAc solution is washed with H2O and brine
  6. dry with materialdried with Na2SO4
  7. filtrationfiltered
  8. customevaporated in vacuo to an off-white solid (1.81 g.)
  9. customRecrystallization from Et2O

Sources & evidence

ORD record
ord-5436978f30974ca890bae131e8657ab9
Source dataset
uspto-grants-1978_07
Patent number
US04099000

Reaction notes

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