N-Hydroxyphthalimide → HCID 18358843, compound

HRID 428381Notes

Reaction equation

HRID 428381 reaction equation
[CH3:1][CH:2]([C:17]([OH:19])=[O:18])[CH2:3][CH2:4][CH2:5][N:6]1[CH:13]=[C:12]([CH2:14][CH2:15][OH:16])[C:10](=[O:11])[NH:9][C:7]1=[O:8].O[N:21]1[C:25](=[O:26])[C:24]2=[CH:27][CH:28]=[CH:29][CH:30]=[C:23]2[C:22]1=[O:31].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[CH3:1][CH:2]([C:17]([OH:19])=[O:18])[CH2:3][CH2:4][CH2:5][N:6]1[CH:13]=[C:12]([CH2:14][CH2:15][O:16][N:21]2[C:22](=[O:31])[C:23]3=[CH:30][CH:29]=[CH:28][CH:27]=[C:24]3[C:25]2=[O:26])[C:10](=[O:11])[NH:9][C:7]1=[O:8]

Participants

6

Reactant 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 69978949HCID 69978949, compound

Product 1

HCID 18358843HCID 18358843, compoundYield 91.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(4-Methylcarboxybutyl)-5-(2-hydroxyethyl)uracil (13.2) no (6.213 g. 23 mmol) was dissolved in anhydrous tetrahydrofuran. N-Hydroxyphthalimide (7.505 g, 46 mmol) and triphenylphosphine (12.046 g, 46 mmol) were added and the solution stirred at ambient temperature. Diethylazodicarboxylate (9.95 g, 57 mmol) was added in 0.5 ml aliquots over 10 minutes, the reaction was then stirred for a further hour. The product was recrystallized twice from chloroform : diethyl ether mixtures to yield 1-(4-methylcarboxybutyl)-5-(2-phthalimidooxyethyl)uracil (13.3) (8.77 g, 91.8%). The structure was confirmed by mass spectroscopy and proton NMR.

Workup

  1. stirringthe reaction was then stirred for a further hour
  2. customThe product was recrystallized twice from chloroform

Sources & evidence

ORD record
ord-8cf71794caa740b2b58e40b764ee3a4b
Source dataset
uspto-grants-2001_11
Patent number
US06313286B1

Reaction notes

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