Triethylamine → HCID 86747110, compound

HRID 2254595Notes

Reaction equation

HRID 2254595 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.ClC(OCC(C)C)=O.[CH2:28]([CH:35]([C:41]([OH:43])=[O:42])[C@@H:36]([C:38]([OH:40])=[O:39])[NH2:37])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C1COCC1.O>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([NH:37][C@H:36]([C:38]([OH:40])=[O:39])[CH:35]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:41]([OH:43])=[O:42])=[O:12])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 8471Triethylamine2×HCID 62365Isobutyl chloroformateHCID 78288N-(tert-butoxycarbonyl)glycineHCID 11665740beta-benzyl-L-aspartic acid

Product 1

HCID 86747110HCID 86747110, compoundYield 60.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

5.3 g (30 mmol) of t-butoxycarbonyl glycine was dissolved in 100 ml of purified THF and 4.6 ml (33 mmol) of triethylamine and 4.33 ml (33 mmol) of isobutyl chloroformate) were added thereto at -15° C. The mixture was stirred at this temperature for 10 minutes. To the resultant solution of a mixed acid anhydride was added a solution which had been prepared by dissolving 8.0 g (36 mmol) of β-benzyl-L-aspartic acid and 5.02 ml (36 mmol) of triethylamine in water and cooling to 0° C. The mixture was then stirred at 0° C. for 1 hour and further at room temperature for 15 hours. After removing the THF by concentration under reduced pressure, cold 10% citric acid was added thereto. The precipitate thus formed was extracted with ethyl acetate twice. The extracts were combined and washed 5 times with one fifth the volume of 5% citric acid and then 10 times with water (one tenth the volume thereof). The solution was dehydrated over anhydrous sodium sulfate and concentrated to dryness. Then the residue was dissolved in ether and precipitated with n-hexane. After repeating this precipitation procedure 3 times, the obtained product was dried, whereby 6.9 g of the titled compound was obtained.

Workup

  1. customat -15° C
  2. customhad been prepared
  3. stirringThe mixture was then stirred at 0° C. for 1 hour and further at room temperature for 15 hours
  4. customAfter removing the THF
  5. concentrationby concentration under reduced pressure, cold 10% citric acid
  6. additionwas added
  7. customThe precipitate thus formed
  8. extractionwas extracted with ethyl acetate twice
  9. washwashed 5 times with one fifth the volume of 5% citric acid
  10. concentrationconcentrated to dryness
  11. dissolutionThen the residue was dissolved in ether
  12. customprecipitated with n-hexane
  13. customthis precipitation procedure 3 times
  14. customthe obtained product was dried

Sources & evidence

ORD record
ord-cde73fa0bbaa44d9946632f88deef49a
Source dataset
uspto-grants-1993_08
Patent number
US05236903

Reaction notes

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