Phthalimide → HCID 90719168, compound

HRID 1242815Notes

Reaction equation

HRID 1242815 reaction equation
[CH3:1][O:2][N:3]=[C:4]1[CH2:8][C@@H:7]([CH2:9]O)[N:6]([C:11]([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:15][CH:14]=2)=[O:12])[CH2:5]1.[C:25]1(=[O:35])[NH:29][C:28](=[O:30])[C:27]2=[CH:31][CH:32]=[CH:33][CH:34]=[C:26]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[C:16]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:15]=[CH:14][C:13]([C:11]([N:6]2[CH2:5][C:4](=[N:3][O:2][CH3:1])[CH2:8][C@H:7]2[CH2:9][N:29]2[C:25](=[O:35])[C:26]3[C:27](=[CH:31][CH:32]=[CH:33][CH:34]=3)[C:28]2=[O:30])=[O:12])=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 58585503HCID 58585503, compound

Product 1

HCID 90719168HCID 90719168, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of alcohol (2) (EZ mixture, 51 mg, 0.16 mmol), phtalimide (70 mg, 0.48 mmol), triphenylphosphine polymer bound (158 mg, 0.48 mmol) and diethyl azodicarboxylate (40% in toluene, 205 μl, 0.48 mmol) in tetrahydrofuran (5 ml) was stirred for 2 days. The resin was filtered off and the reaction mixture was concentrated in vacuo. The crude was purified on silica gel preparative chromatography using DCM as eluant.

Workup

  1. filtrationThe resin was filtered off
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. customThe crude was purified on silica gel preparative chromatography

Sources & evidence

ORD record
ord-9704e2ca356240f8bc2b7042f069ce8d
Source dataset
uspto-grants-2006_10
Patent number
US07115754B2

Reaction notes

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