Tetrahydrofuran → HCID 68530764, compound

HRID 1967421Notes

Reaction equation

HRID 1967421 reaction equation
[NH2:1][N:2]1[C:6](=[O:7])[C:5]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:4]2[C:3]1=[O:12].O1CCCC1.[CH3:18][C:19]([CH3:29])([CH2:27][CH3:28])[CH:20]([CH2:23][C:24](=O)[CH3:25])[CH:21]=O>Cl.C(OCC)(=O)C>[CH3:18][C:19]([C:20]1[CH:23]=[C:24]([CH3:25])[N:1]([N:2]2[C:3](=[O:12])[C:4]3[C:5](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]2=[O:7])[CH:21]=1)([CH3:29])[CH2:27][CH3:28]

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 74645N-AminophthalimideHCID 86642084HCID 86642084, compound

Product 1

HCID 68530764HCID 68530764, compoundYield 77.6%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 8857Ethyl AcetateSolvent

Procedure

N-aminophthalimide (476 mg) and 5N hydrochloric acid (5 drops) were added to the tetrahydrofuran solution (20 mL) of the compound prepared in Example 54 (1 g). The reaction mixture was stirred for 20 minutes under argon gas atmosphere. Ethyl acetate (100 mL) was added to the reaction mixture. The reaction mixture was washed by a saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride. The organic layer was dried with anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by column chromatography on silica gel (Yamazen corporation, high flash 2 L, n-hexane→ethyl acetate/n-hexane=1/4) to obtain the title compound (675 mg) having the following physical data.

Workup

  1. washThe reaction mixture was washed by a saturated aqueous solution of sodium bicarbonate
  2. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe obtained residue was purified by column chromatography on silica gel (Yamazen corporation, high flash 2 L, n-hexane→ethyl acetate/n-hexane=1/4)

Sources & evidence

ORD record
ord-9256487772b84d7da862fb89310362a6
Source dataset
uspto-grants-2013_04
Patent number
US08420810B2

Reaction notes

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