Triethylamine → HCID 53685127, compound

HRID 2413735Notes

Reaction equation

HRID 2413735 reaction equation
Cl.[CH2:2]([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])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(N(CC)CC)C.[CH2:36]([O:43][C:44]([NH:46][CH2:47][C:48](O)=[O:49])=[O:45])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.C(OCC)(=O)C>CN(C)C=O>[CH2:2]([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])[NH:24][C:48](=[O:49])[CH2:47][NH:46][C:44]([O:43][CH2:36][C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)=[O:45])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 8857Ethyl AcetateHCID 14349BenzyloxycarbonylglycineHCID 22827652HCID 22827652, compound

Product 1

HCID 53685127HCID 53685127, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

L-Alanyl-L-prolyl-L-proline benzylester hydrochloride (2.46 g, 6 m mole) was dissolved in dimethylformamide (10 ml) and triethyl amine (0.48 ml, 6 m mole) was added thereto while cooling to neutralize the solution, and then benzyloxycarbonylglycine N-hydroxysuccinimideester (2.02 g, 6.6 m mole) was added thereto. The reaction solution was stirred for 2 days while it had been adjusted to pH around 7 with triethyl amine, and ethyl acetate (150 ml) was added thereto and 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 to give a residue. The thus obtained residue was recrystallized with ethyl acetate to give N-benzyloxycarbonyl glycyl-L-alanyl-L-prolyl-L-proline benzylester (1.3 g). The product as produced above (1.2 g) was dissolved in methanol (50 ml) and then, hydrogen gas was passed through the solution in the presence of palladium-carbon as a catalyst for 3 hours. The catalyst was separated by filtration and the solvent was distilled off. The thus obtained residue was recrystallized with methanol-ether to give glycyl-L-alanyl-L-prolyl-L-proline (688 mg).

Workup

  1. temperaturewhile cooling
  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. customto give a residue
  7. customThe thus obtained residue was recrystallized with ethyl acetate

Sources & evidence

ORD record
ord-82a5e9dd79bf4755890e5212ad27a780
Source dataset
uspto-grants-1988_01
Patent number
US04719200

Reaction notes

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