Bromoacetonitrile → HCID 131736703, compound

HRID 1482300Notes

Reaction equation

HRID 1482300 reaction equation
[CH:1]([N:4](C(C)C)CC)(C)[CH3:2].[Si:10]([O:17][CH:18]([CH2:22][S:23][S:24][C:25]([CH3:28])([CH3:27])[CH3:26])[C:19]([OH:21])=[O:20])([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11].BrCC#N>CN(C=O)C.C(OCC)C>[Si:10]([O:17][CH:18]([CH2:22][S:23][S:24][C:25]([CH3:28])([CH3:27])[CH3:26])[C:19]([O:21][CH2:2][C:1]#[N:4])=[O:20])([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11]

Participants

6

Reactant 3

HCID 11534BromoacetonitrileHCID 81531DiisopropylethylamineHCID 131736700HCID 131736700, compound

Product 1

HCID 131736703HCID 131736703, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

Diisopropylethylamine (98.0 μl, 0.56 mmol) was added to a solution of 2-(tert-butyldimethylsilyloxy)-3-(tert-butyldisulfanyl)propionic acid prepared by the method known in the literature (J. Am. Chem. Soc. 2008, 130, 4919) (Compounds 24, 60.0 mg, 0.185 mmol) and 2-bromoacetonitrile (26.0 μl, 0.373 mmol) in DMF (1.8 ml) at room temperature, and the reaction solution was stirred at the same temperature for 1.5 hours. The reaction mixture was diluted with diethyl ether and washed with a saturated aqueous ammonium chloride solution and brine. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by normal-phase silica gel column chromatography (hexane/ethyl acetate) to afford cyanomethyl 2-(tert-butyldimethylsilyloxy)-3-(tert-butyldisulfanyl)propionate (Compound 25) (48 mg, 71%).

Workup

  1. customprepared by the method
  2. washwashed with a saturated aqueous ammonium chloride solution and brine
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by normal-phase silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-98464fe318f0439d8bfff52e905d93cc
Source dataset
uspto-grants-2016_08
Patent number
US09409952B2

Reaction notes

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