Sodium Hydroxide → HCID 13655171, compound

HRID 745201Notes

Reaction equation

HRID 745201 reaction equation
C([O:3][C:4](=[O:22])[CH2:5][N:6]([C:14](=[O:21])[C@@H:15]1[CH2:19][CH2:18][C:17](=[O:20])[NH:16]1)[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)C.[OH-].[Na+]>CO>[NH:16]1[C:17](=[O:20])[CH2:18][CH2:19][C@H:15]1[C:14]([N:6]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:5][C:4]([OH:22])=[O:3])=[O:21]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13655169HCID 13655169, compound

Product 1

HCID 13655171HCID 13655171, compoundYield 31.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.25 g N-(pyroglutamyl)-N-benzylglycine ethylester is dissolved in 5 ml methanol, treated with 3 ml 2N NaOH, and stirred for 5 min., after which the solution is concentrated to a small volume by removal of solvents. The residue is then dissolved in 10 ml H2O, acidified to pH2, extracted several times with ethyl acetate, and dried over anhydrous MgSO4. Following evaporation of solvent, the residue is chromatographed on silica gel (55 g) using chloroform/methanol/acetic acid (4:1:0.1). The first fractions give 0.36 g N-(pyroglutamyl)-N-benzylglycine as a white solid.

Workup

  1. concentrationafter which the solution is concentrated to a small volume by removal of solvents
  2. dissolutionThe residue is then dissolved in 10 ml H2O
  3. extractionextracted several times with ethyl acetate
  4. dry with materialdried over anhydrous MgSO4
  5. customevaporation of solvent
  6. customthe residue is chromatographed on silica gel (55 g)

Sources & evidence

ORD record
ord-66e1887d86c64e6a9831099b5eeba536
Source dataset
uspto-grants-1986_07
Patent number
US04598067

Reaction notes

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