Glycine → Phenylpropionylglycine

HRID 569849Notes

Reaction equation

HRID 569849 reaction equation
[NH2:1][CH2:2][C:3]([OH:5])=[O:4].[C:6](Cl)(=[O:15])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[OH-].[Na+]>O.CCOCC>[C:9]1([CH2:8][CH2:7][C:6]([NH:1][CH2:2][C:3]([OH:5])=[O:4])=[O:15])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 750GlycineHCID 14798Sodium HydroxideHCID 64801Benzenepropanoyl chloride

Product 1

HCID 152323PhenylpropionylglycineYield 85.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

Glycine (1.5 g, 20 mmol) and hydrocinnamoyl chloride (3.37 g, 22 mmol) were reacted in the presence of NaOH (40 mmol) in a mixture of water and ether using the method described in Example 5 Part A. The crude product was extracted into chloroform, dried (MgSO4) and freed of solvent in vacuo leaving a near white solid (3.53 g, 85%). This was recrystallized from EtOAc (13 ml) to give title compound (2.66 g, 64%) m.p. 112°-114° C.

Workup

  1. extractionThe crude product was extracted into chloroform
  2. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-aac6ae42cbaa4714939bea3604a7c093
Source dataset
uspto-grants-1988_03
Patent number
US04734426

Reaction notes

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