Diphenylacetic Acid → (R)-N5-[Amino(nitroimino) methyl]-N2-(diphenylacetyl)-N-[[4-(hydroxymethyl)-phenyl]methyl]-ornithinamide

HRID 52582

Reaction equation

HRID 52582 reaction equation
[NH2:1][C:2](=[N:21][N+:22]([O-:24])=[O:23])[NH:3][CH2:4][CH2:5][CH2:6][C@H:7]([C:9]([NH:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][OH:20])=[CH:15][CH:14]=1)=[O:10])[NH2:8].[C:25]1([CH:31]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:32](O)=[O:33])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>>[NH2:1][C:2](=[N:21][N+:22]([O-:24])=[O:23])[NH:3][CH2:4][CH2:5][CH2:6][C@H:7]([C:9]([NH:11][CH2:12][C:13]1[CH:14]=[CH:15][C:16]([CH2:19][OH:20])=[CH:17][CH:18]=1)=[O:10])[NH:8][C:32](=[O:33])[CH:31]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

4

Reactant 3

HCID 8333Diphenylacetic AcidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 136381096(R)-N5-[amino(nitroimino)methyl]-N-[[4-(hydroxymethyl)phenyl]methyl]-ornithinamide

Product 1

HCID 136381098(R)-N5-[Amino(nitroimino) methyl]-N2-(diphenylacetyl)-N-[[4-(hydroxymethyl)-phenyl]methyl]-ornithinamideYield 79%

Procedure

Prepared analogously to Example 5f) from (R)-N5 -[amino(nitroimino)methyl]-N-[[4-(hydroxymethyl)phenyl]methyl]-ornithinamide, diphenylacetic acid and TBTU in a yield of 79% of theory.

Sources & evidence

ORD record
ord-51ecce6d508c4e8dacb4d5a3b4e64aac
Source dataset
uspto-grants-1997_04
Patent number
US05616620

Linked notes

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