Phthalimide → HCID 87517306, compound

HRID 2234787Notes

Reaction equation

HRID 2234787 reaction equation
[Cl:1][C:2]1[C:3]2[C:10]([CH2:11][CH:12](O)[CH3:13])=[CH:9][N:8]([C@@H:15]3[O:30][C@H:29]([CH2:31][O:32][CH2:33][C:34]4[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][C:35]=4[Cl:41])[C@@H:18]([O:19][CH2:20][C:21]4[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=4[Cl:28])[C@@:16]3([CH3:42])[OH:17])[C:4]=2[N:5]=[CH:6][N:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:62]1(=[O:72])[NH:66][C:65](=[O:67])[C:64]2=[CH:68][CH:69]=[CH:70][CH:71]=[C:63]12.CCOC(/N=N/C(OCC)=O)=O>C1COCC1.O.C(Cl)Cl>[Cl:1][C:2]1[C:3]2[C:10]([CH2:11][CH:12]([N:66]3[C:62](=[O:72])[C:63]4=[CH:71][CH:70]=[CH:69][CH:68]=[C:64]4[C:65]3=[O:67])[CH3:13])=[CH:9][N:8]([C@@H:15]3[O:30][C@H:29]([CH2:31][O:32][CH2:33][C:34]4[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][C:35]=4[Cl:41])[C@@H:18]([O:19][CH2:20][C:21]4[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=4[Cl:28])[C@@:16]3([CH3:42])[OH:17])[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

8

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 87505693HCID 87505693, compound

Product 1

HCID 87517306HCID 87517306, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of compound 4.3 (1.28 g, 1.89 mmol) in THF (70 mL) were added triphenylphosphine (648 mg, 2.47 mmol) and phthalimide (364.0 mg, 2.47 mmol) followed by DEAD (440 μL, 2.53 mmol), and the solution was stirred for overnight at room temperature. The reaction mixture was diluted by adding 100 mL of CH2Cl2 and water (100 mL) and the aqueous layers extracted three times with CH2Cl2, dried over Na2SO4, filtered and evaporated. The residue obtained was purified by flash column chromatography using 20-30% EtOAc in hexanes as eluent to give the desired compound 4.4 (1.5 g, 100%) as a white solid.

Workup

  1. additionThe reaction mixture was diluted
  2. extractionthe aqueous layers extracted three times with CH2Cl2
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue obtained
  7. customwas purified by flash column chromatography

Sources & evidence

ORD record
ord-5af0f27a33e24681bcd07ece47d98bbb
Source dataset
uspto-grants-2010_05
Patent number
US07713941B2

Reaction notes

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