N-Hydroxyphthalimide → HCID 54196063, compound

HRID 373887Notes

Reaction equation

HRID 373887 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[Si:13]([O:20][CH2:21][CH:22]([OH:33])[CH2:23][CH2:24][P:25](=[O:32])([O:29][CH2:30][CH3:31])[O:26][CH2:27][CH3:28])([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14].O[N:35]1[C:39](=[O:40])[C:38]2=[CH:41][CH:42]=[CH:43][CH:44]=[C:37]2[C:36]1=[O:45].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[Si:13]([O:20][CH2:21][CH:22]([O:33][N:35]1[C:36](=[O:45])[C:37]2=[CH:44][CH:43]=[CH:42][CH:41]=[C:38]2[C:39]1=[O:40])[CH2:23][CH2:24][P:25](=[O:32])([O:26][CH2:27][CH3:28])[O:29][CH2:30][CH3:31])([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]

Participants

6

Reactant 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 19808612Diethyl 4-(t-butyldimethylsilyloxy)-3-hydroxybutylphosphonate

Product 1

HCID 54196063HCID 54196063, compoundYield 70.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diethyl azodicarboxylate (4.02 ml, 0.0.26 mol) was added to a solution of diethyl [4-(t-butyldimethylsilyloxy)-3-hydroxybutyl]phosphonate (7.9 g, 0.023 mol), N-hydroxyphthalimide (3.79 g, 0.023 mol) and triphenylphosphine (6.70 g, 0.026 mol) in dry tetrahydrofuran (100 ml). The mixture was stirred overnight at ambient temperature under a nitrogen atmosphere. The solvent was removed in vacuo and the residue dissolved in diethyl ether and kept at 4° C. for 24 hours. The mixture was filtered and the filtrate evaporated to dryness. The residue was chromatographed on silica gel (hexane-acetone 3:1 as eluant) to give the title compound as a pale yellow oil (7.9 g, 70%). IR:υmax (film) 2990, 2960, 2940, 2860, 1790, 1740, 1605, 1420, 1370, 1250, 1190, 1160, 1120, 1060, 1030, 970, 880, 840, 790, 700 cm-1. 1H NMR: δH (CDCl3) 0.0 (6H, s, SiMe2), 0.8 (9H, s, SiBut), 1.3 (6H, t, J=7Hz, (OCH2CH3)2), 1.78-2.4 (4H, m, CH2CH2P), 3.6-4.1 (7H, m, OCH2CH+(OCH2CH3)2), 7.65-7.95 (4H, m, aromatic H).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue dissolved in diethyl ether
  3. waitkept at 4° C. for 24 hours
  4. filtrationThe mixture was filtered
  5. customthe filtrate evaporated to dryness
  6. customThe residue was chromatographed on silica gel (hexane-acetone 3:1 as eluant)

Sources & evidence

ORD record
ord-dc2eaf4004da4b5584f72fa495467255
Source dataset
uspto-grants-1992_11
Patent number
US05166198

Reaction notes

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