Trifluoroacetic acid → (R)-N5-[Amino(nitroimino)methyl]-N-[(2-thienyl)methyl]-ornithinamide

HRID 52590Notes

Reaction equation

HRID 52590 reaction equation
N(C(OC(C)(C)C)=O)[C@H](C(O)=O)CCCNC(=N)N[N+]([O-])=O.S1C=CC=C1CN.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[NH2:52][C:53](=[N:76][N+:77]([O-:79])=[O:78])[NH:54][CH2:55][CH2:56][CH2:57][C@H:58]([C:67]([NH:69][CH2:70][C:71]1[S:72][CH:73]=[CH:74][CH:75]=1)=[O:68])[NH:59]C(OC(C)(C)C)=O.FC(F)(F)C(O)=O>>[NH2:52][C:53](=[N:76][N+:77]([O-:79])=[O:78])[NH:54][CH2:55][CH2:56][CH2:57][C@H:58]([C:67]([NH:69][CH2:70][C:71]1[S:72][CH:73]=[CH:74][CH:75]=1)=[O:68])[NH2:59]

Participants

6

Reactant 5

HCID 6422Trifluoroacetic acidHCID 34005(2-Thienylmethyl)amineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 136381109(R)-N5-[amino(nitroimino)methyl]-N2-[(tert.-butyloxy)carbonyl]-N-[(2-thienyl)methyl]-ornithinamideHCID 178454200HCID 178454200, compound

Product 1

HCID 136381108(R)-N5-[Amino(nitroimino)methyl]-N-[(2-thienyl)methyl]-ornithinamide

Procedure

First of all Boc-Arg(NO2)-OH was reacted with thiophene-2-methanamine and TBTU as in Example 8a). The resulting (R)-N5 -[amino(nitroimino)methyl]-N2 -[(tert.-butyloxy)carbonyl]-N-[(2-thienyl)methyl]-ornithinamide was then reacted, without purification, with trifluoroacetic acid as in Example 23b). The crude product obtained in a quantitative yield was further processed without purification.

Sources & evidence

ORD record
ord-1c1598767bea497387d3419ad8b568de
Source dataset
uspto-grants-1997_04
Patent number
US05616620

Reaction notes

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