Phthaloyl chloride → Phthalimide

HRID 876637Notes

Reaction equation

HRID 876637 reaction equation
C([N:3](CC)CC)C.[C:8](Cl)(=[O:18])[C:9]1[C:10](=[CH:14][CH:15]=[CH:16][CH:17]=1)[C:11](Cl)=[O:12]>CN(C1C=CN=CC=1)C.ClCCl.C(OCC)(=O)C>[C:8]1(=[O:18])[NH:3][C:11](=[O:12])[C:10]2=[CH:14][CH:15]=[CH:16][CH:17]=[C:9]12

Participants

6

Reactant 2

HCID 6955Phthaloyl chlorideHCID 8471Triethylamine

Product 1

HCID 6809Phthalimide

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of MCH17-1 (520 mg), triethyl amine (0.82 mL) and DMAP (24 mg) in 10 mL dichloromethane at 0° C. was added phthaloyl chloride (0.36 mL). The mixture was stirred overnight at rt, diluted with ethyl acetate and washed with 1N HCl, aq. NaHCO3 and brine. It was dried over anhydrous MgSO4, filtered, concentrated and purified by chromatography eluting with 0% to 50% ethyl acetate in hexane to provide 338 mg of phthalimide protected intermediate which was stirred with 5 mL of trifluoroacetic acid at rt for 40 min. The reaction mixture was evaporated to dryness, the residue was suspended in aq. NaHCO3 and extracted 3× with ethyl acetate. The combined organic layer was washed with brine, dried over MgSO4, filtered and evaporated to dryness to obtain 220 mg MCH 17-2.

Workup

  1. washwashed with 1N HCl, aq. NaHCO3 and brine
  2. dry with materialIt was dried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by chromatography
  6. washeluting with 0% to 50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-1acc5ff0f4514bf784b4042a85dd5bbb
Source dataset
uspto-grants-2015_03
Patent number
US08987242B2

Reaction notes

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