N-Hydroxyphthalimide → HCID 178454078, compound

HRID 439881Notes

Reaction equation

HRID 439881 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>C1C=CC=CC=1>[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 178418813HCID 178418813, compound

Product 1

HCID 178454078HCID 178454078, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A solution of 12 ml (0.0718 mol) of diethyl azodicarboxylate (93%) in 80 ml of benzene is added dropwise to a mixture of 14.62 g (0.06791 mol) of cis-4-(N-BOC-amino)-cyclohexanol, 11.1 g (0.068 mol) of N-hydroxyphthalimide, 17.84 g (0.068 mol) of triphenylphosphine and 600 ml of benzene at 20°-30° C., while stirring. The reaction mixture is further stirred at room temperature for 15 hours and then evaporated in vacuo. The residue is purified by flash chromatography on silica gel of particle size 0.04-0.063 mm using methylene chloride. After evaporation of the product-containing fractions, the title compound is obtained as a crystalline residue, m.p. 207°-208° C.

Workup

  1. stirringThe reaction mixture is further stirred at room temperature for 15 hours
  2. customevaporated in vacuo
  3. customThe residue is purified by flash chromatography on silica gel of particle size 0.04-0.063 mm
  4. customAfter evaporation of the product-containing fractions

Sources & evidence

ORD record
ord-705261334c394fae86d5200f66499bf8
Source dataset
uspto-grants-1996_05
Patent number
US05516806

Reaction notes

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