Trifluoroacetic acid → (R)-N5-[amino(nitroimino)methyl]-N-[[4-(hydroxymethyl)phenyl]methyl]-ornithinamide

HRID 52581Notes

Reaction equation

[NH2:1][C:2](=[N:28][N+:29]([O-:31])=[O:30])[NH:3][CH2:4][CH2:5][CH2:6][C@H:7]([C:16]([NH:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][OH:27])=[CH:22][CH:21]=1)=[O:17])[NH:8]C(OC(C)(C)C)=O.FC(F)(F)C(O)=O>>[NH2:1][C:2](=[N:28][N+:29]([O-:31])=[O:30])[NH:3][CH2:4][CH2:5][CH2:6][C@H:7]([C:16]([NH:18][CH2:19][C:20]1[CH:21]=[CH:22][C:23]([CH2:26][OH:27])=[CH:24][CH:25]=1)=[O:17])[NH2:8]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 136381097HCID 136381097, compound

Product 1

HCID 136381096(R)-N5-[amino(nitroimino)methyl]-N-[[4-(hydroxymethyl)phenyl]methyl]-ornithinamideYield 83%

Procedure

Prepared analogously to Example 23b) from (R)-N5 -[amino(nitroimino)methyl]-N2 -(tert.-butoxycarbonyl)-N-[[4-(hydroxymethyl)phenyl]methyl]-ornithinamide by the action of trifluoroacetic acid in a yield of 83% of theory.

Sources & evidence

ORD record: ord-f4581c94ac384280b3988e675612bb08
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05616620

Reaction notes

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