N-Hydroxyphthalimide → HCID 19917924, compound

HRID 1755843Notes

Reaction equation

HRID 1755843 reaction equation
N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH:32][N:33]1[C:37](=[O:38])[C:36]2=[CH:39][CH:40]=[CH:41][CH:42]=[C:35]2[C:34]1=[O:43].[CH2:44]([O:51][C:52]1[C:53](=[O:60])[CH:54]=[C:55]([CH2:58]O)[O:56][CH:57]=1)[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1>O1CCCC1>[CH2:44]([O:51][C:52]1[C:53](=[O:60])[CH:54]=[C:55]([CH2:58][O:32][N:33]2[C:34](=[O:43])[C:35]3=[CH:42][CH:41]=[CH:40][CH:39]=[C:36]3[C:37]2=[O:38])[O:56][CH:57]=1)[C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=1

Participants

6

Reactant 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 9015985-(benzyloxy)-2-(hydroxymethyl)-4H-pyran-4-one

Product 1

HCID 19917924HCID 19917924, compoundYield 72.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diethyl azodicarboxylate (16.68 g) (86 mmol) are dissolved in 1200 ml of absolute tetrahydrofuran. Thereto there is added a mixture consisting of 22.6 g (86 mmol) of triphenylphosphine, 14.1 g (86 mmol) of N-hydroxyphthalimide and 20.0 g (86 mmol) of 5-(benzyloxy)-2-(hydroxymethyl)-4H-pyran-4-one (known from J. Med. Chem. 17, 1, 1974). After stirring at room temperature for 20 hours the mixture is filtered and the filter material is rinsed with ethanol. The filtrate and rinse solution are combined and concentrated, and the residue is crystallized using ethanol. After repeated recrystallization from ethanol there are obtained 23.5 g of N-[[5-(benzyloxy)-4-oxo-4H-pyran-2-yl]methoxy]phthalimide as white crystals of m.p. 172° C.

Workup

  1. additionThereto there is added a mixture
  2. filtrationis filtered
  3. washthe filter material is rinsed with ethanol
  4. washThe filtrate and rinse solution
  5. concentrationconcentrated
  6. customthe residue is crystallized
  7. customrecrystallization from ethanol

Sources & evidence

ORD record
ord-0d746ffb76e5448f982478fe6cd35525
Source dataset
uspto-grants-1995_08
Patent number
US05438052

Reaction notes

Loading…