N,N'-di-Boc-2-methanesulfonyloxy-1,3-diaminopropane → di-tert-butyl [2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-1,3-propanediyl]biscarbamate

HRID 459613Notes

Reaction equation

HRID 459613 reaction equation
CS(O[CH:6]([CH2:16][NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:7][NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])(=O)=O.[K].[C:26]1(=[O:36])[NH:30][C:29](=[O:31])[C:28]2=[CH:32][CH:33]=[CH:34][CH:35]=[C:27]12>O>[O:31]=[C:29]1[C:28]2[C:27](=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:26](=[O:36])[N:30]1[CH:6]([CH2:16][NH:17][C:18](=[O:19])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:7][NH:8][C:9](=[O:10])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13]

Participants

4

Reactant 2

HCID 14839452N,N'-di-Boc-2-methanesulfonyloxy-1,3-diaminopropaneHCID 24194345Phthalimide potassium salt

Product 1

HCID 86597870di-tert-butyl [2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-1,3-propanediyl]biscarbamateYield 73.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of 2-[(tert-butoxycarbonyl)amino]-1-{[(tert-butoxycarbonyl)amino]methyl}ethyl methanesulfonate (200 g) was added phthalimide potassium salt (101 g), and the mixture was stirred overnight at 75° C. To the reaction mixture was added water (6 L), and the mixture was extracted with ethyl acetate (6 L). The organic layer was washed with water (1.5 L×3) and brine, and dried over anhydrous magnesium sulfate. Concentration under reduced pressure gave a residue, which was triturated with hexane (500 ml). The collected crystals was washed with hexane (100 ml×3), and the mother liquor was recrystallized from hexane (300 ml) and combined with the former crystals to give di-tert-butyl [2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-1,3-propanediyl]biscarbamate (168 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate (6 L)
  2. washThe organic layer was washed with water (1.5 L×3) and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationConcentration under reduced pressure
  5. customgave a residue, which
  6. customwas triturated with hexane (500 ml)
  7. washThe collected crystals was washed with hexane (100 ml×3)
  8. customthe mother liquor was recrystallized from hexane (300 ml)

Sources & evidence

ORD record
ord-0aa79b8be54f41d191f27f450e673f28
Source dataset
uspto-grants-2007_03
Patent number
US07192943B2

Reaction notes

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