Triethylamine → 2-(N-t-Butoxycarbonyl-N-methylamino)-4-(4-t-butoxycarbonylamino-3,5-dimethylphenoxy)nitrobenzene

HRID 1358583Notes

Reaction equation

HRID 1358583 reaction equation
[C:1]([O:5][C:6]([N:8]([C:10]1[CH:15]=[C:14]([O:16][C:17]2[CH:22]=[C:21]([CH3:23])[C:20]([NH2:24])=[C:19]([CH3:25])[CH:18]=2)[CH:13]=[CH:12][C:11]=1[N+:26]([O-:28])=[O:27])[CH3:9])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:29]([O:33][C:34](=O)[O:35]C(C)(C)C)([CH3:32])([CH3:31])[CH3:30].C(N(CC)CC)C>O1CCCC1>[C:1]([O:5][C:6]([N:8]([C:10]1[CH:15]=[C:14]([O:16][C:17]2[CH:18]=[C:19]([CH3:25])[C:20]([NH:24][C:34]([O:33][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:35])=[C:21]([CH3:23])[CH:22]=2)[CH:13]=[CH:12][C:11]=1[N+:26]([O-:28])=[O:27])[CH3:9])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) esterHCID 181849972-(N-t-Butoxycarbonyl-N-methylamino)-4-(4-amino-3,5-dimethylphenoxy)nitrobenzene

Product 1

HCID 181849432-(N-t-Butoxycarbonyl-N-methylamino)-4-(4-t-butoxycarbonylamino-3,5-dimethylphenoxy)nitrobenzeneYield 60.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-(N-t-butoxycarbonyl-N-methylamino)-4-(4-amino-3,5-dimethylphenoxy)nitrobenzene (2.27 g), di-t-butylcarbonate (1.28 g),triethylamine (0.59 g) and anhydrous tetrahydrofuran (20 ml) was heated at reflux for 6 hours. The reaction mixture was concentrated and the residue was partitioned between ethyl acetate and water. The extract was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was chromatographed on a silica gel column using hexane: ethyl acetate=10:1 as the eluant to afford the title compound (1.74 g, mp 154-156° C. ).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 6 hours
  3. concentrationThe reaction mixture was concentrated
  4. customthe residue was partitioned between ethyl acetate and water
  5. dry with materialThe extract was dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was chromatographed on a silica gel column

Sources & evidence

ORD record
ord-20e231105814409a998cbd2cc4ea8a6f
Source dataset
uspto-grants-2003_07
Patent number
US06596751B2

Reaction notes

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