O-Methyltyramine → N5-[Amino(nitroimino)methyl]-N2-(diphenylacetyl)-N-[2-(4-methoxyphenyl)ethyl]-ornithinamide

HRID 52595

Reaction equation

HRID 52595 reaction equation
[NH2:1][C:2](=[N:27][N+:28]([O-:30])=[O:29])[NH:3][CH2:4][CH2:5][CH2:6][C@H:7]([C:24](O)=[O:25])[NH:8][C:9](=[O:23])[CH:10]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[CH3:31][O:32][C:33]1[CH:38]=[CH:37][C:36]([CH2:39][CH2:40][NH2:41])=[CH:35][CH:34]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>>[NH2:1][C:2](=[N:27][N+:28]([O-:30])=[O:29])[NH:3][CH2:4][CH2:5][CH2:6][C@@H:7]([C:24]([NH:41][CH2:40][CH2:39][C:36]1[CH:37]=[CH:38][C:33]([O:32][CH3:31])=[CH:34][CH:35]=1)=[O:25])[NH:8][C:9](=[O:23])[CH:10]([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 3

HCID 4657O-MethyltyramineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 136381100(R)-N5-[amino(nitroimino)methyl]-N2-(diphenylacetyl)-ornithine

Product 1

HCID 136381113N5-[Amino(nitroimino)methyl]-N2-(diphenylacetyl)-N-[2-(4-methoxyphenyl)ethyl]-ornithinamideYield 47%

Procedure

Prepared analogously to Example 8a) from (R)-N5 -[amino(nitroimino)methyl]-N2 -(diphenylacetyl)-ornithine, 4-methoxybenzenethanamine and TBTU in a yield of 47% of theory.

Sources & evidence

ORD record
ord-e9a0414aba054e69bac783df1acedb20
Source dataset
uspto-grants-1997_04
Patent number
US05616620

Linked notes

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