Sodium Hydroxide → HCID 13655171, compound

HRID 2231816Notes

Reaction equation

HRID 2231816 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. TLC: (silica gel; CHCl3 /MeOH/HOAC=4:1:0.1) Rf =0.6, Mass: 276 (molecular ion).

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-2d456553bd4c43b2b327f9f2783cb050
Source dataset
uspto-grants-1988_11
Patent number
US04785003

Reaction notes

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