HCID 178418361, compound → HCID 178429592, compound

HRID 2058119Notes

Reaction equation

HRID 2058119 reaction equation
[ClH:1].C([NH:12][C@H:13]([C:21]([NH:23][C:24]1[CH:33]=[C:32]2[C:27]([C:28]([CH3:35])=[CH:29][C:30](=[O:34])[O:31]2)=[CH:26][CH:25]=1)=[O:22])[CH2:14][CH2:15][CH2:16][NH:17][C:18](=[NH:20])[NH2:19])(OCC1C=CC=CC=1)=[O:3].[H][H]>CO.C(O)(=O)C.O.[C].[Pd]>[OH2:3].[ClH:1].[NH2:12][C@H:13]([C:21]([NH:23][C:24]1[CH:33]=[C:32]2[C:27]([C:28]([CH3:35])=[CH:29][C:30](=[O:34])[O:31]2)=[CH:26][CH:25]=1)=[O:22])[CH2:14][CH2:15][CH2:16][NH:17][C:18](=[NH:19])[NH2:20].[NH2:12][C@H:13]([C:21]([NH:23][C:24]1[CH:33]=[C:32]2[C:27]([C:28]([CH3:35])=[CH:29][C:30](=[O:34])[O:31]2)=[CH:26][CH:25]=1)=[O:22])[CH2:14][CH2:15][CH2:16][NH:17][C:18](=[NH:19])[NH2:20].[ClH:1]

Participants

7

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178429591HCID 178429591, compound

Product 1

HCID 178429592HCID 178429592, compoundYield 100%

Reagents, catalysts & solvents 4

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

7-(Nα -carbobenzoxy-L-arginyl)amino-4-methyl-coumarin hydrochloric acid salt (251 mg, 0.5 mM) was dissolved in a mixture of methyl alcohol (50 ml), acetic acid (5 ml) and water (10 ml), and 5% palladium-carbon catalyst (25 mg) was added thereto. This mixture was stirred while being treated with hydrogen gas at room temperature. The catalyst was removed by filtration, and from the filtrate the solvent was distilled off under reduced pressure. To the residue ether (50 ml) was added and the precipitated powder was separated by filtration to give 7-L-arginylamino-4-methylcoumarin hydrochloric acid salt hemihydrate (188 mg, yield: 100%).

Workup

  1. additionwas added
  2. customThe catalyst was removed by filtration
  3. distillationfrom the filtrate the solvent was distilled off under reduced pressure
  4. additionTo the residue ether (50 ml) was added
  5. customthe precipitated powder was separated by filtration

Sources & evidence

ORD record
ord-f85acb7d771d402eb773d89c4acd0612
Source dataset
uspto-grants-1980_07
Patent number
US04215047

Reaction notes

Loading…