O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate → (R)-N5-[Amino(nitroimino)methyl]-N2-(diphenylacetyl)-N-[[4-(methylaminosulphonylmethyl)phenyl]methyl]-ornithinamide

HRID 1952990Notes

Reaction equation

HRID 1952990 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][NH:32][S:33]([CH2:36][C:37]1[CH:42]=[CH:41][C:40]([CH2:43][NH2:44])=[CH:39][CH:38]=1)(=[O:35])=[O:34].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:44][CH2:43][C:40]1[CH:41]=[CH:42][C:37]([CH2:36][S:33]([NH:32][CH3:31])(=[O:35])=[O:34])=[CH:38][CH:39]=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:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 3

HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 91674254-(Aminomethyl)-N-methylbenzenemethanesulfonamideHCID 136381100(R)-N5-[amino(nitroimino)methyl]-N2-(diphenylacetyl)-ornithine

Product 1

HCID 136333683(R)-N5-[Amino(nitroimino)methyl]-N2-(diphenylacetyl)-N-[[4-(methylaminosulphonylmethyl)phenyl]methyl]-ornithinamideYield 70%

Procedure

Prepared analogously to Example 6d) from (R)-N5 -[amino(nitroimino)methyl]-N2 -(diphenylacetyl)-ornithine, 4-(methylamino-sulphonylmethyl)benzenemethanamine and TBTU in a yield of 70% of theory. Colourless amorphous substance.

Sources & evidence

ORD record
ord-85dd0bbb756244879b2a0c83dcea36ed
Source dataset
uspto-grants-2000_09
Patent number
US06114390

Reaction notes

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