(1S)-1-(4-Nitrophenyl)ethan-1-amine → N-(4-Carbamimidoyl-phenyl)-N'-[1-(4-nitro-phenyl)-ethyl]-2-phenyl-malonamide

HRID 479605Notes

Reaction equation

HRID 479605 reaction equation
[Na].[C:2]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:23])[CH:13]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:14]([OH:16])=O)=[CH:7][CH:6]=1)(=[NH:4])[NH2:3].[B-](F)(F)(F)F.CCOC(C(C#N)=NOC(N(C)C)=[N+](C)C)=O.[N+:46]([C:49]1[CH:54]=[CH:53][C:52]([C@@H:55]([NH2:57])[CH3:56])=[CH:51][CH:50]=1)([O-:48])=[O:47]>CN(C=O)C>[C:2]([C:5]1[CH:6]=[CH:7][C:8]([NH:11][C:12](=[O:23])[CH:13]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:14]([NH:57][CH:55]([C:52]2[CH:51]=[CH:50][C:49]([N+:46]([O-:48])=[O:47])=[CH:54][CH:53]=2)[CH3:56])=[O:16])=[CH:9][CH:10]=1)(=[NH:4])[NH2:3]

Participants

5

Reactant 3

HCID 1268055(1S)-1-(4-Nitrophenyl)ethan-1-amineHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 69657777N-(4-Carbamimidoyl-phenyl)-2-phenyl-malonamic sodium

Product 1

HCID 15907897N-(4-Carbamimidoyl-phenyl)-N'-[1-(4-nitro-phenyl)-ethyl]-2-phenyl-malonamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

75 mg (0.235 mmol) of the sodium salt from example 2 were dissolved in 2.5 ml DMF. 85 mg (0.265 mmol) TOTU in 2.5 ml DMF were added and stirred for 30 min at rt. Then 34 μl (0.265 mmol) NEM and 53.7 mg (0.265 mmol) of (S)-1-(4-nitrophenyl)-ethylamine in 0.5 ml of DMF was added and the mixture stirred at rt overnight. After filtration, the filtrate was evaporated to dryness and purified by prep. RP-HPLC.

Workup

  1. stirringthe mixture stirred at rt overnight
  2. filtrationAfter filtration
  3. customthe filtrate was evaporated to dryness
  4. custompurified by prep

Sources & evidence

ORD record
ord-5376f9ae4650406ca39735c57c93337b
Source dataset
uspto-grants-2003_11
Patent number
US06645992B2

Reaction notes

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