Bis(4-nitrophenyl) carbonate → HCID 42625373, compound

HRID 1174157Notes

Reaction equation

HRID 1174157 reaction equation
[C:1]([O:5][C:6]([C@@H:8]([NH:13][CH2:14][CH2:15][NH:16][CH2:17][C:18]1[N:23]=[C:22]([C:24]([O:26][CH3:27])=[O:25])[CH:21]=[CH:20][CH:19]=1)[C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:28](=O)(OC1C=CC([N+]([O-])=O)=CC=1)[O:29]C1C=CC([N+]([O-])=O)=CC=1.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([C@@H:8]([N:13]1[CH2:14][CH2:15][N:16]([CH2:17][C:18]2[N:23]=[C:22]([C:24]([O:26][CH3:27])=[O:25])[CH:21]=[CH:20][CH:19]=2)[C:28]1=[O:29])[C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 78756Bis(4-nitrophenyl) carbonateHCID 516892Sodium BicarbonateHCID 67407119HCID 67407119, compound

Product 1

HCID 42625373HCID 42625373, compoundYield 85.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
25 °C

Procedure

A solution of the product from Example 17C (10.27 g, 27.1 mmol), bis (4-nitrophenyl) carbonate (8.24 g, 27.1 mmol), in toluene (100 mL) was heated at 110° C. for 16 hours, cooled to 25° C., treated with 1M sodium bicarbonate, and extracted with ethyl acetate. The organic phase layer was concentrated and the residue was purified by flash chromatography on silica gel eluting with 60% ethyl acetate in hexane to give the title compound as a white solid (9.44 g, 64% yield).

Workup

  1. extractionextracted with ethyl acetate
  2. concentrationThe organic phase layer was concentrated
  3. customthe residue was purified by flash chromatography on silica gel eluting with 60% ethyl acetate in hexane

Sources & evidence

ORD record
ord-f5c16bfaa423478eb1cf319a79780a24
Source dataset
uspto-grants-2010_11
Patent number
US07834043B2

Reaction notes

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