Dimethylformamide → HCID 54065956, compound

HRID 2413737Notes

Reaction equation

HRID 2413737 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:31]([CH2:34][CH3:35])CC)C.[C:36]([O:39][CH2:40][CH3:41])(=[O:38])C.CN(C)[CH:44]=[O:45]>>[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:44](=[O:45])[C@H:34]([CH2:35][C:8]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[NH:31][C:36]([O:39][CH2:40][C:41]1[CH:13]=[CH:14][CH:15]=[CH:11][CH:10]=1)=[O:38])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 8471Triethylamine2×HCID 8857Ethyl AcetateHCID 22827652HCID 22827652, compound

Product 1

HCID 54065956HCID 54065956, compound

Procedure

L-alanyl-L-prolyl-L-proline benzylester hydrochloride (2.46 g, 6 m mole) was dissolved in dimethylformamide (10 ml), and triethylamine (0.84 ml, 6 m mole) was added thereto under cooling to neutralize it. Benzyloxycarbonyl-L-phenylalanine N-hydroxysuccinimide ester (2.62 g, 6.6 m mole) was added thereto. The reaction solution was stirred for 2 days while it had bean adjusting to pH around 7 with triethylamine, and then ethyl acetate (150 ml) was added thereto. The mixture 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 residue was recrystallized with ethyl acetate to give N-benzyloxycarbonyl-L-phenylalanyl-L-alanyl-L-prolyl-L-proline benzylester (3.2 g). The product as produced above (3 g) was dissolved in methanol (100 ml) and hydrogen gas was passed through the solution in the presence of palladium-carbon as a catalyst for 5 hours. The catalyst was separated by filtration and the solvent was distilled off from the filtrate. The thus obtained residue was recrystallized with methanolether to give L-phenylalanyl-L-alanyl-L-prolyl-L-proline (1.4 g).

Workup

  1. temperatureunder cooling
  2. washThe mixture was washed with 1N hydrochloric acid, 5% aqueous sodium bicarbonate, and water in order
  3. dry with materialThe ethyl acetate layer was dried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe thus obtained residue was recrystallized with ethyl acetate

Sources & evidence

ORD record
ord-08fc639acc5e440a886032f15ddd770e
Source dataset
uspto-grants-1988_01
Patent number
US04719200

Reaction notes

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