Bromoacetonitrile → HCID 89668391, compound

HRID 1482180Notes

Reaction equation

HRID 1482180 reaction equation
Br[CH2:2][C:3]#[N:4].C(N(C(C)C)C(C)C)C.[CH:14]([S:17][C:18](=[O:31])[CH2:19][C@H:20]([NH:24][C:25](=[O:30])[CH2:26][CH2:27][CH:28]=[CH2:29])[C:21]([OH:23])=[O:22])([CH3:16])[CH3:15].[Cl-].[NH4+]>CN(C=O)C>[CH:14]([S:17][C:18](=[O:31])[CH2:19][C@H:20]([NH:24][C:25](=[O:30])[CH2:26][CH2:27][CH:28]=[CH2:29])[C:21]([O:23][CH2:2][C:3]#[N:4])=[O:22])([CH3:16])[CH3:15]

Participants

6

Reactant 4

HCID 11534BromoacetonitrileHCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 89668332HCID 89668332, compound

Product 1

HCID 89668391HCID 89668391, compoundYield 70.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Bromoacetonitrile (0.510 ml, 7.32 mmol) and N-ethyl-N-isopropylpropan-2-amine (0.153 ml, 0.878 mmol) were added to a solution of (S)-4-(isopropylthio)-4-oxo-2-(pent-4-enamido)butanoic acid (Compound 1f-IB) (200 mg, 0.732 mmol) in DMF (1 ml), and the mixture was stirred at room temperature for 30 minutes. A saturated aqueous ammonium chloride solution (1 ml) was added to the reaction mixture, after which the mixture was extracted with ethyl acetate and the organic layer was washed with water. The organic extract was then dried over magnesium sulfate. Following concentration under reduced pressure, the resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=100/0→60/40) to afford (S)-cyanomethyl 4-(isopropylthio)-4-oxo-2-(pent-4-enamido)butanoate (Compound 1g-IB) (161 mg, 70%).

Workup

  1. extractionafter which the mixture was extracted with ethyl acetate
  2. washthe organic layer was washed with water
  3. extractionThe organic extract
  4. dry with materialwas then dried over magnesium sulfate
  5. concentrationconcentration under reduced pressure
  6. customthe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=100/0→60/40)

Sources & evidence

ORD record
ord-d3cd5b0e7442479ba33764e23b95e5f8
Source dataset
uspto-grants-2016_08
Patent number
US09409952B2

Reaction notes

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