N-Hydroxyphthalimide → HCID 11388071, compound

HRID 1639408Notes

Reaction equation

HRID 1639408 reaction equation
[CH:1]([O:14][N:15]1[CH:20]=[C:19]([O:21][CH:22]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:18](=[O:35])[CH:17]=[C:16]1[CH2:36][OH:37])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[N:39]1[C:43](=[O:44])[C:42]2=[CH:45][CH:46]=[CH:47][CH:48]=[C:41]2[C:40]1=[O:49].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N+](C(OCC)=O)(C(OCC)=O)=[N-]>CN(C)C=O.O.C(OCC)(=O)C.O1CCCC1>[C:43]1(=[O:44])[N:39]([O:37][CH2:36][C:16]2[N:15]([O:14][CH:1]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH:20]=[C:19]([O:21][CH:22]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:18](=[O:35])[CH:17]=2)[C:40](=[O:49])[C:41]2=[CH:48][CH:47]=[CH:46][CH:45]=[C:42]12

Participants

9

Reactant 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 117521734(1H)-Pyridinone, 1,5-bis(diphenylmethoxy)-2-(hydroxymethyl)-HCID 14357405Diethyldiazodicarboxylate

Product 1

HCID 11388071HCID 11388071, compoundYield 50.2%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

12.3 g (0.0251 mol) of the product of Step (3) was added and dissolved in dimethylformamide (125 ml). Then, dried tetrahydrofuran (250 ml), 4.1 g (0.0251 mol) of N-hydroxyphthalimide and 9.9 g (0.0376 mol) of triphenylphosphine were added thereto. Further, 5.8 ml (0.0377 mol) of diethyl diazodicarboxylate was dropwise added under cooling with ice. The mixture was stirred at the same temperature for 10 minutes, and then ethyl acetate (500 ml) and water (1,500 ml) were added thereto. The ethyl acetate layer was washed with water and a saturated sodium chloride solution, and then dried over anhydrous magnesium sulfate, and then concentrated to dryness. The residue was subjected to silica gel column chromatography and eluted by benzene/ethyl acetate (4/1) to obtain 8.0 g of the above identified compound (yield: 50.2%)

Workup

  1. temperatureunder cooling with ice
  2. washThe ethyl acetate layer was washed with water
  3. dry with materiala saturated sodium chloride solution, and then dried over anhydrous magnesium sulfate
  4. concentrationconcentrated to dryness
  5. washeluted by benzene/ethyl acetate (4/1)
  6. customto obtain 8.0 g of the

Sources & evidence

ORD record
ord-ef7dacb53b054a78a5366da21258d5e1
Source dataset
uspto-grants-1989_11
Patent number
US04883879

Reaction notes

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