N-Hydroxyphthalimide → HCID 178454077, compound

HRID 439882Notes

Reaction equation

HRID 439882 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[C:13]([NH:20][C@H:21]1[CH2:26][CH2:25][C@H:24]([OH:27])[CH2:23][CH2:22]1)([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].O[N:29]1[C:33](=[O:34])[C:32]2=[CH:35][CH:36]=[CH:37][CH:38]=[C:31]2[C:30]1=[O:39].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[C:13]([NH:20][C@@H:21]1[CH2:22][CH2:23][C@H:24]([O:27][N:29]2[C:33](=[O:34])[C:32]3[C:31](=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:30]2=[O:39])[CH2:25][CH2:26]1)([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14]

Participants

6

Reactant 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 178418329HCID 178418329, compound

Product 1

HCID 178454077HCID 178454077, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4.1 ml (0.0244 mol) of diethyl azodicarboxylate (93%) are added dropwise to a mixture of 5 g (0.0232 mol) of trans-4-(N-BOC-amino)-cyclohexanol (cf. Example 1c), 3.8 g (0.0232 mol) of N-hydroxyphthalimide, 6.1 g (0.0232 mol) of triphenylphosphine and 100 ml of tetrahydrofuran at 20°-30° C. The reaction mixture is further stirred at room temperature for 15 hours and then evaporated in vacuo. To separate off the diethyl 1,2-hydrazinc dicarboxylate and triphenylphosphine oxide, the oily residue is dissolved in ethyl acetate, the solution is cooled to 0° C. and filtered, the filtrate is evaporated and the same operation is repeated once more, but using diethyl ether. The residue obtained after evaporation of the diethyl ether is purified by means of flash chromatography on silica gel using ethyl acetate/hexane mixtures (1:2 and 1:1). After evaporation of the product-containing fractions, the title compound is obtained as a crystalline residue, m.p. 134°-135° C.

Workup

  1. customevaporated in vacuo
  2. customTo separate off the diethyl 1,2-hydrazinc dicarboxylate and triphenylphosphine oxide
  3. dissolutionthe oily residue is dissolved in ethyl acetate
  4. temperaturethe solution is cooled to 0° C.
  5. filtrationfiltered
  6. customthe filtrate is evaporated
  7. customThe residue obtained
  8. customafter evaporation of the diethyl ether
  9. customis purified by means of flash chromatography on silica gel
  10. customAfter evaporation of the product-containing fractions

Sources & evidence

ORD record
ord-8c81186254c44510abb3e7d587e71009
Source dataset
uspto-grants-1996_05
Patent number
US05516806

Reaction notes

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