Phthalimide → HCID 86634372, compound

HRID 1191273Notes

Reaction equation

HRID 1191273 reaction equation
[N:1]([CH2:4][C@@H:5]1[C@H:9](O)[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].[C:18]1(=[O:28])[NH:22][C:21](=[O:23])[C:20]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:19]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.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]([N:22]2[C:18](=[O:28])[C:19]3[C:20](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:21]2=[O:23])[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 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 86634371HCID 86634371, compound

Product 1

HCID 86634372HCID 86634372, compoundYield 50.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the compound 5 (658 mg) in tetrahydrofuran (15 mL), phthalimide (600 mg), triphenylphosphine (1070 mg) and 2.2 mol/L of a solution (2.0 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 (508 mg) 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-1d8314d226d44a1c95f35e6ee003f087
Source dataset
uspto-grants-2014_03
Patent number
US08680092B2

Reaction notes

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