4-Nitrobenzoic Acid → HCID 86634369, compound

HRID 1191271Notes

Reaction equation

HRID 1191271 reaction equation
[N:1]([CH2:4][C@@H:5]1[C@@H:9]([OH:10])[CH2:8][CH2:7][N:6]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[N+:2]=[N-:3].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N+:37]([C:40]1[CH:48]=[CH:47][C:43]([C:44](O)=[O:45])=[CH:42][CH:41]=1)([O-:39])=[O:38].N(C(OCC)=O)=NC(OCC)=O>O1CCCC1.C1(C)C=CC=CC=1.O>[N:1]([CH2:4][C@@H:5]1[C@@H:9]([O:10][C:44]([C:43]2[CH:42]=[CH:41][C:40]([N+:37]([O-:39])=[O:38])=[CH:48][CH:47]=2)=[O:45])[CH2:8][CH2:7][N:6]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[N+:2]=[N-:3]

Participants

8

Reactant 4

HCID 61084-Nitrobenzoic AcidHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 86634370HCID 86634370, compound

Product 1

HCID 86634369HCID 86634369, compoundYield 58.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the compound 3 (1.30 g) in tetrahydrofuran (25 mL), triphenylphosphine (3.10 g), 4-nitrobenzoic acid (2.24 g) and 2.2 mol/L of a solution (5.4 mL) of diethyl azodicarboxylate in toluene were added at 0° C. The reaction mixture was stirred at room temperature for overnight. The reaction mixture was added water and extracted with ethyl acetate. The extract was washed with aqueous saturated sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate and then concentrated. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:0→4:1) to obtain the title compound (1.22 g) having the following physical properties.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with aqueous saturated sodium hydrogen carbonate solution and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:0→4:1)

Sources & evidence

ORD record
ord-6f2ff5c419e44c2e9441d306982b38b7
Source dataset
uspto-grants-2014_03
Patent number
US08680092B2

Reaction notes

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