Acetonitrile → N-(1-methyl-1-(3-(N'-nitroguanidino)phenyl)ethyl)carbamic acid t-butyl ester

HRID 1861899Notes

Reaction equation

HRID 1861899 reaction equation
[C:1]([O:5][C:6](=[O:18])[NH:7][C:8]([CH3:17])([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([NH2:16])[CH:11]=1)[CH3:9])([CH3:4])([CH3:3])[CH3:2].C(#N)C.C[N:23](N=O)[C:24]([NH:26][N+:27]([O-:29])=[O:28])=N.C(N(CC)CC)C>C(O)(=O)C>[C:1]([O:5][C:6](=[O:18])[NH:7][C:8]([CH3:9])([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([NH:16][C:24]([NH2:23])=[N:26][N+:27]([O-:29])=[O:28])[CH:11]=1)[CH3:17])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 229810903-[2-(Boc-amino)-2-propyl]anilineHCID 135436526N-Methyl-N'-nitro-N-nitrosoguanidine

Product 1

HCID 136388333N-(1-methyl-1-(3-(N'-nitroguanidino)phenyl)ethyl)carbamic acid t-butyl esterYield 54.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of the compound (145 mg) obtained in Example 2, acetonitrile (10 ml), N-methyl-N′-nitro-N-nitrosoguanidine (85 mg), triethylamine (0.08 ml) and acetic acid (0.03 ml) was stirred at room temperature for 16 h. The reaction mixture was concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography (eluent, n-hexane:ethyl acetate=1:1) to give 106 mg of the titled compound (yield, 54%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe resulting residue was purified by silica gel column chromatography (eluent, n-hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-e59ac0eb1179415c884cc6eaa0f3b10f
Source dataset
uspto-grants-2003_03
Patent number
US06534546B1

Reaction notes

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