Phthalimide → HCID 59954332, compound

HRID 1976243Notes

Reaction equation

HRID 1976243 reaction equation
O[C@H:2]1[CH2:37][N:5]2[C:6]3[C:11]([N:12]([C:14](=[O:36])[C:15]4[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:35])[C:23]5[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=5[C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=5)=[CH:17][CH:16]=4)[CH2:13][C@@H:4]2[CH2:3]1)=[CH:10][CH:9]=[CH:8][CH:7]=3.[C:38]1(=[O:48])[NH:42][C:41](=[O:43])[C:40]2=[CH:44][CH:45]=[CH:46][CH:47]=[C:39]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>CN(C)C=O>[C:29]1([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[C:22]([NH:21][C:18]2[CH:17]=[CH:16][C:15]([C:14]([N:12]3[C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[N:5]4[CH2:37][C@@H:2]([N:42]5[C:41](=[O:43])[C:40]6=[CH:44][CH:45]=[CH:46][CH:47]=[C:39]6[C:38]5=[O:48])[CH2:3][C@H:4]4[CH2:13]3)=[O:36])=[CH:20][CH:19]=2)=[O:35])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 15545387HCID 15545387, compound

Product 1

HCID 59954332HCID 59954332, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of (2R,3aS)-2-hydroxy-5-[4-[(2-phenylbenzoyl)amino]benzoyl]-1,2,3,3a,4,5-hexahydro-pyrrolo[1,2-a]quinoxaline (1.2 g) prepared in Example 3, phthalimide (0.54 g) and triphenyl phosphine (0.96 g) in anhydrous N,N-dimethylformamide (10 ml), there was gradually dropwise added, under ice-cooling, a solution of diisopropyl azodicarboxylate (0.74 g) in anhydrous N,N-dimethylformamide (4 ml). After stirring the reaction solution at room temperature for 2 hours, it was poured into ice water and then extracted with ethyl acetate. The resulting organic phase was washed with water, dried over anhydrous magnesium sulfate and then concentrated. The resulting residue was subjected to silica gel column chromatography and then eluted with hexane/ethyl acetate (1/1) to give 1.1 g (yield 73.0%) of the title compound as amorphous powder.

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. washThe resulting organic phase was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. washeluted with hexane/ethyl acetate (1/1)

Sources & evidence

ORD record
ord-1313f24a5a804d698535dd25be7b54ca
Source dataset
uspto-grants-2001_05
Patent number
US06225306B1

Reaction notes

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