N-Hydroxyphthalimide → HCID 178454091, compound

HRID 439885Notes

Reaction equation

HRID 439885 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[C:13]([NH:20][C@@H:21]1[CH2:24][C@H:23]([CH2:25][OH:26])[CH2:22]1)([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].O[N:28]1[C:32](=[O:33])[C:31]2=[CH:34][CH:35]=[CH:36][CH:37]=[C:30]2[C:29]1=[O:38].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1C=CC=CC=1>[C:13]([NH:20][C@@H:21]1[CH2:24][C@H:23]([CH2:25][O:26][N:28]2[C:32](=[O:33])[C:31]3[C:30](=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:29]2=[O:38])[CH2:22]1)([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14]

Participants

6

Reactant 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 178454088HCID 178454088, compound

Product 1

HCID 178454091HCID 178454091, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A solution of 6.54 ml (0.0391 mol) of diethyl azodicarboxylate (93%) in 30 ml of benzene is added dropwise to a mixture of 7.5 g (0.03726 mol) of cis-3-(N-BOC-amino)-cyclobutanemethanol, 6.08 g (0.03726 mol) of N-hydroxyphthalimide, 9.774 g (0.03726 mol) of triphenylphosphine and 120 ml of benzene at 20°-30° C., while stirring. The reaction mixture is stirred at room temperature for 2 hours and filtered, the crystalline residue (diethyl 1,2-hydrazinedicarboxylate) is washed with benzene and the filtrate is evaporated in vacuo. The residue is purified by means of flash chromatography on silica gel using ethyl acetate/hexane mixtures (1:3 and 1:2). After evaporation of the product-containing fractions and recrystallization of the residue from ethyl acetate/hexane, the title compound is obtained, m.p. 131.5°-132.5° C.

Workup

  1. stirringThe reaction mixture is stirred at room temperature for 2 hours
  2. filtrationfiltered
  3. washthe crystalline residue (diethyl 1,2-hydrazinedicarboxylate) is washed with benzene
  4. customthe filtrate is evaporated in vacuo
  5. customThe residue is purified by means of flash chromatography on silica gel
  6. customAfter evaporation of the product-containing fractions and recrystallization of the residue from ethyl acetate/hexane

Sources & evidence

ORD record
ord-753aad562f484445909e219727b8498e
Source dataset
uspto-grants-1996_05
Patent number
US05516806

Reaction notes

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