Trifluoroacetic acid → HCID 137231656, compound

HRID 52599Notes

Reaction equation

[NH2:1][C:2](=[N:29][N+:30]([O-:32])=[O:31])[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]([O:26][CH2:27][CH3:28])=[CH:22][CH:21]=1)=[O:17])[NH:8]C(OC(C)(C)C)=O.[F:33][C:34]([F:39])([F:38])[C:35]([OH:37])=[O:36].[OH-].[Na+]>>[NH2:1][C:2](=[N:29][N+:30]([O-:32])=[O:31])[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]([O:26][CH2:27][CH3:28])=[CH:24][CH:25]=1)=[O:17])[NH2:8].[F:33][C:34]([F:39])([F:38])[C:35]([O-:37])=[O:36]

Participants

Reactant 3

HCID 6422Trifluoroacetic acid

HCID 14798Sodium Hydroxide

HCID 137231655HCID 137231655, compound

Product 1

HCID 137231656HCID 137231656, compoundYield 70%

Procedure

Prepared analogously to Example 5e) from (R)-N5 -[amino(nitroimino)methyl]-N2 -[(tert.-butyloxy)carbonyl]-N-[(4-ethoxyphenyl)methyl]-ornithinamide by the action of trifluoroacetic acid in a yield of 70% of theory. The base liberated from the salt by treatment with 1N sodium hydroxide solution melted at 182°-184° C. (ethyl acetate).

Sources & evidence

ORD record: ord-0e47177b57e3422fa256272dff76bd63
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05616620

Reaction notes

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