Water → tert-butyl N-[3-(tert-butoxycarbonylamino)-2-cyano-propyl]carbamate

HRID 459624Notes

Reaction equation

HRID 459624 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.[C-:25]#[N:26].[Na+].O>CS(C)=O>[C:25]([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])#[N:26]

Participants

5

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 14839452N,N'-di-Boc-2-methanesulfonyloxy-1,3-diaminopropane

Product 1

HCID 375633tert-butyl N-[3-(tert-butoxycarbonylamino)-2-cyano-propyl]carbamateYield 49.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a stirred solution of 2-[(tert-butoxycarbonyl)amino]-1-{[(tert-butoxycarbonyl)amino]methyl}ethyl methanesulfonate (10 g) in dimethyl sulfoxide (100 ml) was added sodium cyanide (2 g) at room temperature and the whole mixture was stirred overnight at room temperature. Water was added to the reaction mixture and the whole mixture was extracted with ethyl acetate. The extract was washed with water and brine and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the residual oil was purified by column chromatography on silica gel (ethyl acetate:hexane=1:5) to give di-tert-butyl (2-cyano-1,3-propanediyl)biscarbamate (4.04 g).

Workup

  1. extractionthe whole mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residual oil was purified by column chromatography on silica gel (ethyl acetate:hexane=1:5)

Sources & evidence

ORD record
ord-e61cafdd80254853a34ac8f52eff97d4
Source dataset
uspto-grants-2007_03
Patent number
US07192943B2

Reaction notes

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