Methanol → HCID 178476707, compound

HRID 1953002Notes

Reaction equation

HRID 1953002 reaction equation
[NH2:1][C:2]([NH:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][NH:15][C:16](=[O:44])[C@@H:17]([CH2:34][CH2:35][CH2:36][NH:37][C:38]([NH2:43])=[N:39][N+]([O-])=O)[NH:18][C:19](=[O:33])[CH:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:10][CH:9]=1)=[N:3][C:4]#[N:5].C[OH:46]>[Pd]>[NH2:1][C:2]([NH:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][NH:15][C:16](=[O:44])[C@@H:17]([CH2:34][CH2:35][CH2:36][NH:37][C:38](=[NH:39])[NH2:43])[NH:18][C:19](=[O:33])[CH:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:10][CH:9]=1)=[N:3][C:4]#[N:5].[C:19]([O-:33])(=[O:46])[CH3:20]

Participants

4

Reactant 2

HCID 887MethanolHCID 178512371HCID 178512371, compound

Product 1

HCID 178476707HCID 178476707, compoundYield 5.9%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Prepared analogously to Example 1d) from (R)-N-[[4-[[[amino-(cyanoimino)methyl]amino]methyl]phenyl]methyl]-N5 -[amino(nitroimino)methyl]-N2 -(diphenylacetyl)-ornithinamide by catalytic hydrogenation in the presence of palladium/activated charcoal and using methanol as solvent. After final purification by column chromatography on silica gel (Macherey-Nagel, 0.063-0.2 mm) using n-butanol/glacial acetic acid/water=4/1/1 (v/v/v) as eluant, the desired compound is obtained as a colourless, amorphous-glassy substance in a yield of 5.9% of theory.

Workup

  1. customAfter final purification by column chromatography on silica gel (Macherey-Nagel, 0.063-0.2 mm)

Sources & evidence

ORD record
ord-bc9227754ede41128aedafacf13fc81c
Source dataset
uspto-grants-2000_09
Patent number
US06114390

Reaction notes

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