Ethyl Acetate → HCID 54487623, compound

HRID 2413734Notes

Reaction equation

HRID 2413734 reaction equation
Cl.C([O:9][C:10](=[O:28])[C@@H:11]1[CH2:15][CH2:14][CH2:13][N:12]1[C:16](=[O:27])[C@@H:17]1[CH2:21][CH2:20][CH2:19][N:18]1[C:22](=[O:26])[C@H:23]([CH3:25])[NH2:24])C1C=CC=CC=1.ON1[C:34]2[CH:35]=[CH:36][CH:37]=C[C:33]=2[N:32]=N1.CN(C)CCCN=C=NCC.C(OCC)(=[O:52])C>CN(C)C=O>[NH:32]1[CH2:33][CH2:34][CH2:35][C@H:36]1[C:37]([NH:24][C@H:23]([C:22]([N:18]1[CH2:19][CH2:20][CH2:21][C@H:17]1[C:16]([N:12]1[CH2:13][CH2:14][CH2:15][C@H:11]1[C:10]([OH:9])=[O:28])=[O:27])=[O:26])[CH3:25])=[O:52]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 22827652HCID 22827652, compound

Product 1

HCID 54487623HCID 54487623, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

L-alanyl-L-prolyl-L-proline benzylester hydrochloride (2.46 g, 6 m mole), benzyloxcarbonyl-L-proline (1.65 g, 6.6 m mole) and 1-hydroxybenzotriazole (0.9 g, 6.6 m mole) were dissolved in dimethylformamide (6 ml) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (1.2 ml, 6.6 m mole) was added thereto at -15° C. The mixture was stirred for 16 hours at room temperature and to the reaction solution, ethyl actate was added. The solution was washed with 1N hydrochloric acid, 5% aqueous sodium bicarbonate and water in order. The ethyl acetate layer was dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The thus obtained oily residue was dissolved in methanol-water (4:1, 25 ml and hydrogen gas was passed through the solution in the presence of palladium carbon as a catalyst for 2 hours. The catalyst was separated by filtration and the solvent was distilled off under reduced pressure. The thus obtained residue was recrystallized with methanol-ether to give L-prolyl-L-alanyl-L-prolyl-L-proline (1.48 g).

Workup

  1. customat -15° C
  2. additionwas added
  3. washThe solution was washed with 1N hydrochloric acid, 5% aqueous sodium bicarbonate and water in order
  4. dry with materialThe ethyl acetate layer was dried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. dissolutionThe thus obtained oily residue was dissolved in methanol-water (4:1, 25 ml and hydrogen gas
  7. customThe catalyst was separated by filtration
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe thus obtained residue was recrystallized with methanol-ether

Sources & evidence

ORD record
ord-e8e5efbe628a4299b3c8996aab1914cd
Source dataset
uspto-grants-1988_01
Patent number
US04719200

Reaction notes

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