Bromoacetonitrile → (S)-cyanomethyl 4-(benzylthio)-4-oxo-2-(pent-4-enamido)butanoate

HRID 1482178Notes

Reaction equation

HRID 1482178 reaction equation
Br[CH2:2][C:3]#[N:4].C(N(C(C)C)C(C)C)C.[CH2:14]([S:21][C:22](=[O:35])[CH2:23][C@H:24]([NH:28][C:29](=[O:34])[CH2:30][CH2:31][CH:32]=[CH2:33])[C:25]([OH:27])=[O:26])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[Cl-].[NH4+]>CS(C)=O>[CH2:14]([S:21][C:22](=[O:35])[CH2:23][C@H:24]([NH:28][C:29](=[O:34])[CH2:30][CH2:31][CH:32]=[CH2:33])[C:25]([O:27][CH2:2][C:3]#[N:4])=[O:26])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 11534BromoacetonitrileHCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 89668400(S)-4-(benzylthio)-4-oxo-2-(pent-4-enamido)butanoic acid

Product 1

HCID 89668255(S)-cyanomethyl 4-(benzylthio)-4-oxo-2-(pent-4-enamido)butanoateYield 79%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2-Bromoacetonitrile (4.35 ml, 62.4 mmol) and N-ethyl-N-isopropylpropan-2-amine (0.651 ml, 3.74 mmol) were added to a solution of (S)-4-(benzylthio)-4-oxo-2-(pent-4-enamido)butanoic acid (Compound 1f-ID) (1.00 g, 3.12 mmol) in DMSO (4.35 ml), and the mixture was stirred at room temperature for 40 minutes. A saturated aqueous ammonium chloride solution (5 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→40/60) to afford (S)-cyanomethyl 4-(benzylthio)-4-oxo-2-(pent-4-enamido)butanoate (Compound 1g-ID) (885.2 mg, 79%).

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→40/60)

Sources & evidence

ORD record
ord-d1ae13e0b23a4bbead6acef18cdc290e
Source dataset
uspto-grants-2016_08
Patent number
US09409952B2

Reaction notes

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