Glycolic Acid → HCID 13344954, compound

HRID 1462237Notes

Reaction equation

HRID 1462237 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N:21]([CH2:28]OC(=O)C(C)(C)C)[C:22]3[N:27]=[CH:26][CH:25]=[CH:24][N:23]=3)=[CH:17][CH:16]=2)[C:10](=[O:36])[C:9]1=[O:37])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:38]([OH:42])(=[O:41])[CH2:39][OH:40].Cl.C(O)C>C(OCC)(=O)C>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N:21]([CH2:28][O:40][CH2:39][C:38]([OH:42])=[O:41])[C:22]3[N:23]=[CH:24][CH:25]=[CH:26][N:27]=3)=[CH:17][CH:16]=2)[C:10](=[O:36])[C:9]1=[O:37])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 757Glycolic AcidHCID 13210503HCID 13210503, compoundHCID 21887872Ethanol hydrochloride

Product 1

HCID 13344954HCID 13344954, compoundYield 52.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

In 30 ml of ethyl acetate was dissolved 1 g of 1-benzyl-4-{4-[N-pivaloyloxymethyl-N-(2-pyrimidinyl)-amino]benzyl}-2,3-dioxopiperazine, and 1 g of glycolic acid and 0.02 ml of N hydrogen chloride-ethanol solution were added, after which the resulting mixture was subjected to reaction at room temperature for 3 hours with stirring. After the completion of the reaction, the solvent was removed by distillation under reduced pressure, and the residue thus obtained was extracted with 100 ml of methylene chloride. The methylene chloride layer was washed with 30 ml of water and then 30 ml of saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate, after which the solvent was removed by distillation under reduced pressure. The residue thus obtained was purified by a column chromatography (Wakogel C-200, eluted with chloroformethanol), and recrystallized from ethyl acetate-diisopropyl ether, to obtain 0.5 g (52.8% yield) of 1-benzyl-4-{4-[N-carboxymethoxymethyl-N-(2-pyrimidinyl)amino]benzyl}-2,3-dioxopiperazine having a melting point of 85° to 90° C.

Workup

  1. additionwere added
  2. customafter which the resulting mixture was subjected to reaction at room temperature for 3 hours
  3. customAfter the completion of the reaction
  4. customthe solvent was removed by distillation under reduced pressure
  5. customthe residue thus obtained
  6. extractionwas extracted with 100 ml of methylene chloride
  7. washThe methylene chloride layer was washed with 30 ml of water
  8. dry with material30 ml of saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate
  9. customafter which the solvent was removed by distillation under reduced pressure
  10. customThe residue thus obtained
  11. customwas purified by a column chromatography (Wakogel C-200, eluted with chloroformethanol)
  12. customrecrystallized from ethyl acetate-diisopropyl ether

Sources & evidence

ORD record
ord-40508d78a0c34cefa67c057da49c6def
Source dataset
uspto-grants-1984_07
Patent number
US04459407

Reaction notes

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