Ethyl Acetate → HCID 12800846, compound

HRID 1679185Notes

Reaction equation

HRID 1679185 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, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

p-Nitrobenzyl glycinate hydrobromide (7.15 g., 24.6 mMol) is suspended in H2O (15 ml.) and the mixture is layered with EtOAc (40 ml.). The mixture is cooled in ice and stirred while cold, saturated aqueous K2CO3 (6 ml.) is added. The layers are separated and the aqueous portion is extracted with more EtOAc (3 × 15 ml.). The combined EtOAc solution is dried over Na2SO4, filtered and evaporated in vacuo to provide p-nitrobenzyl glycinate (5.05 g., 24.0 mMol, 98% yield) as an off-white solid.

Workup

  1. temperatureThe mixture is cooled in ice
  2. additionis added
  3. customThe layers are separated
  4. extractionthe aqueous portion is extracted with more EtOAc (3 × 15 ml.)
  5. dry with materialThe combined EtOAc solution is dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-85288bfa059f40b0938c92bc24766210
Source dataset
uspto-grants-1978_03
Patent number
US04079179

Reaction notes

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