Acetic Anhydride → HCID 69247967, compound

HRID 475038Notes

Reaction equation

HRID 475038 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].C1COCC1.[NH2:13][C:14]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:15]=1[C:16](=[O:36])[N:17]([CH:24]1[CH2:29][CH2:28][C:27](=[O:30])[N:26]([CH2:31][CH2:32][O:33][CH3:34])[C:25]1=[O:35])[C:18]2=[O:23]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:34][O:33][CH2:32][CH2:31][N:26]1[C:27](=[O:30])[CH2:28][CH2:29][CH:24]([N:17]2[C:18](=[O:23])[C:19]3[C:15](=[C:14]([NH:13][C:1](=[O:3])[CH3:2])[CH:22]=[CH:21][CH:20]=3)[C:16]2=[O:36])[C:25]1=[O:35]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8028TetrahydrofuranHCID 69247466HCID 69247466, compound

Product 1

HCID 69247967HCID 69247967, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Acetic anhydride (0.5 mL) and DMAP (3 mg) were added to a THF solution of 4-amino-2-(1-(2-methoxyethyl)-2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione (50 mg). The reaction mixture was allowed to react for 8 hrs at room temperature. Then, DCM (15 mL) were added and solvents were removed by rotary evaporation in vacuo. The residue was washed with 0.5 N aqueous hydrochloric acid, saturated sodium bicarbonate, and brine, dried over anhydrous magnesium sulfate, and filtered. Pale white solid (38 mg) was obtained after removal of solvent by rotary evaporation in vacuo. MS (m/e): 374 (M+H).

Workup

  1. customto react for 8 hrs at room temperature
  2. customsolvents were removed by rotary evaporation in vacuo
  3. washThe residue was washed with 0.5 N aqueous hydrochloric acid, saturated sodium bicarbonate, and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered

Sources & evidence

ORD record
ord-25880604558f41dd99ad24d460eaf9da
Source dataset
uspto-grants-2014_01
Patent number
US08637545B2

Reaction notes

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