Water → [2-(4-di-n-propylamino-butyl)-1,3-dioxo-2,3-dihydro-1H-isoindol-5-ylmethyl]-carbamic acid t-butyl ester

HRID 2080729Notes

Reaction equation

HRID 2080729 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[C:12]([C:19]([OH:21])=O)[C:13](=[CH:17][CH:18]=1)[C:14]([OH:16])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:22]([N:25]([CH2:31][CH2:32][CH3:33])[CH2:26][CH2:27][CH2:28][CH2:29][NH2:30])[CH2:23][CH3:24].O>C1(C)C(C)=CC=CC=1>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][C:10]1[CH:11]=[C:12]2[C:13](=[CH:17][CH:18]=1)[C:14](=[O:16])[N:30]([CH2:29][CH2:28][CH2:27][CH2:26][N:25]([CH2:31][CH2:32][CH3:33])[CH2:22][CH2:23][CH3:24])[C:19]2=[O:21])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 7138396N,N-dipropylbutane-1,4-diamineHCID 230792094-[(Boc-amino)methyl]-phthalic acid

Product 1

HCID 66941653[2-(4-di-n-propylamino-butyl)-1,3-dioxo-2,3-dihydro-1H-isoindol-5-ylmethyl]-carbamic acid t-butyl esterYield 49.2%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent2×

Procedure

The compound (123 mg) obtained in Example 7-4 was dissolved in xylene (5.0 ml). A xylene solution (5.0 ml) containing the compound (83.4 mg) obtained in Example 1-2 was dropped to the solution and the whole was refluxed under heating for 63 hours. The solution was added with water to stop the reaction and then subjected to extraction with chloroform. The organic layer was washed with water and a saturated saline solution, followed by drying with anhydrous sodium sulfate. The residue obtained by distilling the solvent off was then purified through silica gel column chromatography (hexane/ethyl acetate), thereby obtaining the subject compound (88.4 mg) as a yellow solid.

Workup

  1. additionwas dropped to the solution
  2. temperaturethe whole was refluxed
  3. temperatureunder heating for 63 hours
  4. customthe reaction
  5. extractionsubjected to extraction with chloroform
  6. washThe organic layer was washed with water
  7. dry with materialby drying with anhydrous sodium sulfate
  8. customThe residue obtained
  9. distillationby distilling the solvent
  10. customoff was then purified through silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-53ac96361f5b40e3874e407376766ce2
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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