HCID 178418361, compound → HCID 178429588, compound

HRID 2058123Notes

Reaction equation

HRID 2058123 reaction equation
[ClH:1].[C:2]([O:6][C:7]([NH:9][C@H:10]([C:20]([NH:22][CH2:23][C:24]([NH:26][C@H:27]([C:35]([NH:37][C:38]1[CH:47]=[C:46]2[C:41]([C:42]([CH3:49])=[CH:43][C:44](=[O:48])[O:45]2)=[CH:40][CH:39]=1)=[O:36])[CH2:28][CH2:29][CH2:30][NH:31][C:32](=[NH:34])[NH2:33])=[O:25])=[O:21])[CH2:11][O:12]CC1C=CC=CC=1)=[O:8])([CH3:5])([CH3:4])[CH3:3].[H][H]>CO.[C].[Pd].C(O)(=O)C>[ClH:1].[C:2]([O:6][C:7]([NH:9][C@H:10]([C:20]([NH:22][CH2:23][C:24]([NH:26][C@H:27]([C:35]([NH:37][C:38]1[CH:47]=[C:46]2[C:41]([C:42]([CH3:49])=[CH:43][C:44](=[O:48])[O:45]2)=[CH:40][CH:39]=1)=[O:36])[CH2:28][CH2:29][CH2:30][NH:31][C:32](=[NH:33])[NH2:34])=[O:25])=[O:21])[CH2:11][OH:12])=[O:8])([CH3:5])([CH3:3])[CH3:4]

Participants

6

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178429587HCID 178429587, compound

Product 1

HCID 178429588HCID 178429588, compoundYield 66.9%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

7-(Nα -tert-butyloxycarbonyl-O-benzyl-L-serylglycyl-L-arginyl)amino-4-methylcoumarin hydrochloric acid salt (120 mg, 0.28 mM) was dissolved in methyl alcohol (50 ml), and palladium-carbon catalyst (20 mg) was added. Through this mixture hydrogen gas was passed for 4 hours with stirring. The catalyst was removed by filtration and the filtrate was concentrted to yield a solid material. The residue was dissolved in acetic acid (10 ml) and lyophilized to give 7-(Nα-tert-butyloxycarbonyl-L-serylglycyl-L-arginyl)amino-4-methylcoumarin hydrochloric acid salt [X] (70 mg).

Workup

  1. customThe catalyst was removed by filtration
  2. customto yield a solid material

Sources & evidence

ORD record
ord-3cedf37f67c74d16b389d2e1f05e2c83
Source dataset
uspto-grants-1980_07
Patent number
US04215047

Reaction notes

Loading…