Triethylamine → HCID 18602841, compound

HRID 485590Notes

Reaction equation

HRID 485590 reaction equation
[ClH:1].[CH3:2][O:3][C:4](=[O:14])[C@@H:5]1[CH2:9][CH2:8][CH2:7][N:6]1[C:10](=[O:13])[CH2:11][NH2:12].[CH2:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:17][C:16]1=O.C(N(CC)CC)C.[Na]>CO>[ClH:1].[CH3:2][O:3][C:4](=[O:14])[C@@H:5]1[CH2:9][CH2:8][CH2:7][N:6]1[C:10](=[O:13])[CH2:11][NH:12][CH:16]1[CH2:15][C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:17]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 119832-IndanoneHCID 5360545SodiumHCID 13890216HCID 13890216, compound

Product 1

HCID 18602841HCID 18602841, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Glycyl-L-proline methylester hydrochloride (16.0 g, 72.1 m mole) was dissolved in methanol (150 ml), and Indan-2-on (4.75 g, 36.0 m mole) and triethylamine (1.8 g, 18.0 m mole) were added thereto. Sodium syanoborohydride (2.27 g, 36.0 m mole) was gradually added thereto while cooling with ice and stirring. The mixture was stirred for 1 hour while cooling with ice and next for 5 hours at room temperature. A little insoluble material was separated by filtration, and the filtrate was concentrated under reduced pressure. To the residue, water (100 ml) and ethyl ether (100 ml) were added, and the solution was adjusted to pH 1.5 with 6N hydrochloric acid while stirring to dissolve it. The ethyl ether layer was removed, and the remaining water layer was washed with ethyl ether (100 ml). The desired product was extracted from the water layer with chloroform (100 ml×3 times). The thus obtained chloroform as extracted was concentrated under reduced pressure. To thus produced tar-like residue ethyl ether and 5% sodium bicarbonate (200 ml) were added and the mixture was stirred to dissolve the solid matter. The aqueous layer was removed and the ethyl ether layer was washed with aqueous solution saturated with sodium chloride. To the ethyl ether layer water (150 ml) was added, and the solution was adjusted to pH 1.5 with 6N hydrochloric acid while stirring and ethyl ether was removed. The water layer was washed with ethyl ether (100 ml) and to the water layer chloroform (200 ml) was added. The solution was adjusted to pH 8.0 with sodium bicarbonate while stirring. The aqueous layer was removed, and chloroform layer was dried with anhydrous sodium sulfate, and the sodium sulfate was sepa rated by filtration. Separately, anhydrous hydrogen chloride gas was brown into the chloroform, and thus obtained hydrogen chloride chloroform solution was added to the above mentioned chloroform layer. After checking the solution acidic enough, the chloroform was removed off under reduced pressure, to yield N-(2-indanyl) glycyl-L-proline methylester hydrochloride (4.50 g, 13.3 m mole, yield: 37%).

Workup

  1. temperaturewhile cooling with ice
  2. stirringThe mixture was stirred for 1 hour
  3. customA little insoluble material was separated by filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. additionTo the residue, water (100 ml) and ethyl ether (100 ml) were added
  6. stirringwhile stirring
  7. dissolutionto dissolve it
  8. customThe ethyl ether layer was removed
  9. washthe remaining water layer was washed with ethyl ether (100 ml)
  10. extractionThe desired product was extracted from the water layer with chloroform (100 ml×3 times)
  11. extractionThe thus obtained chloroform as extracted
  12. concentrationwas concentrated under reduced pressure
  13. additionTo thus produced tar-like residue ethyl ether and 5% sodium bicarbonate (200 ml) were added
  14. stirringthe mixture was stirred
  15. dissolutionto dissolve the solid matter
  16. customThe aqueous layer was removed
  17. washthe ethyl ether layer was washed with aqueous solution saturated with sodium chloride
  18. additionTo the ethyl ether layer water (150 ml) was added
  19. stirringwhile stirring
  20. customethyl ether was removed
  21. washThe water layer was washed with ethyl ether (100 ml) and to the water layer chloroform (200 ml)
  22. additionwas added
  23. stirringwhile stirring
  24. customThe aqueous layer was removed
  25. dry with materialchloroform layer was dried with anhydrous sodium sulfate
  26. filtrationthe sodium sulfate was sepa rated by filtration
  27. additionwas added to the
  28. customthe chloroform was removed off under reduced pressure

Sources & evidence

ORD record
ord-80e69f9d04d94e849389ef77531673ff
Source dataset
uspto-grants-1985_08
Patent number
US04536395

Reaction notes

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