Citric Acid → HCID 7154480, compound

HRID 1981927Notes

Reaction equation

HRID 1981927 reaction equation
C[O:2][C:3](=[O:28])[CH2:4][NH:5][C:6](=[O:27])[C@H:7]([CH2:23][CH:24]([CH3:26])[CH3:25])[NH:8][C:9](=[O:22])[C@@H:10]1[CH2:14][CH2:13][CH2:12][N:11]1[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16].[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO>[C:18]([O:17][C:15]([N:11]1[CH2:12][CH2:13][CH2:14][C@H:10]1[C:9]([NH:8][C@H:7]([C:6]([NH:5][CH2:4][C:3]([OH:28])=[O:2])=[O:27])[CH2:23][CH:24]([CH3:26])[CH3:25])=[O:22])=[O:16])([CH3:20])([CH3:21])[CH3:19]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 13605337HCID 13605337, compound

Product 1

HCID 7154480HCID 7154480, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The thus obtained N-t-butoxycarbonyl-prolylleucyl-glycine methyl ester in an amount of 294.6 g was dissolved in 1.6 l of methanol. To this, 1.6 l of 1N-NaOH was added dropwise with ice cooling and the reaction was carried out at room temperature for 2 hours. Subsequently, 20% citric acid was added dropwise to the reaction mixture to make the pH 3 to 4. Then, the whole reaction mixture was extracted with 5 l of ethyl acetate, and the extract was washed well with 5% citric acid solution and saturated sodium chloride aqueous solution, and dried. After removing the solvent by distillation, a white solid was obtained. The resulting solid of N-t-butoxycarbonyl-prolyl-leucyl-glycine was purified by washing with petroleum ether. Yield: 269.3 g (94.7%). Melting point 87°-90° C. [α]D20 =-80.5° (C=1, ethanol). Rf =0.46 (TLC, chloroform: methanol: acetic acid =95:5:3 by volume).

Workup

  1. customThen, the whole reaction mixture
  2. extractionwas extracted with 5 l of ethyl acetate
  3. washthe extract was washed well with 5% citric acid solution and saturated sodium chloride aqueous solution
  4. customdried
  5. customAfter removing the solvent
  6. distillationby distillation
  7. customa white solid was obtained
  8. customThe resulting solid of N-t-butoxycarbonyl-prolyl-leucyl-glycine was purified
  9. washby washing with petroleum ether
  10. customMelting point 87°-90° C. [α]D20 =-80.5° (C=1, ethanol)

Sources & evidence

ORD record
ord-c7e0c887f7a846858ebb163e280586c3
Source dataset
uspto-grants-1986_06
Patent number
US04594409

Reaction notes

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