Water → HCID 18956023, compound

HRID 866475Notes

Reaction equation

HRID 866475 reaction equation
Cl.[NH2:2][CH2:3][C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)=[O:5].O.C([O-])([O-])=O.[K+].[K+]>CCOC(C)=O>[NH2:2][CH2:3][C:4]([O:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]([O:14][CH3:15])=[CH:12][CH:13]=1)=[O:5]

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 18956022HCID 18956022, compound

Product 1

HCID 18956023HCID 18956023, compoundYield 89.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of p-methoxybenzyl glycinate hydrochloride (23.2 g., 0.1 mole), H2O (50 ml.), and EtOAc (150 ml.) is stirred vigorously with ice-bath cooling while an ice-cold, saturated aqueous solution of K2CO3 (25 ml.) is added. The aqueous phase is separated and extracted with more EtOAc (2 × 50 ml.). The combined EtOAc solution is dried with MgSO4, filtered, evaporated in vacuo, and stripped with PhH to provide p-methoxybenzyl glycinate (17.4 g.) as a pale yellow liquid.

Workup

  1. additionis added
  2. customThe aqueous phase is separated
  3. extractionextracted with more EtOAc (2 × 50 ml.)
  4. dry with materialThe combined EtOAc solution is dried with MgSO4
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-7eb8a191b2594aa1a2268f3caa647c8b
Source dataset
uspto-grants-1978_07
Patent number
US04099000

Reaction notes

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