Bromoacetonitrile → HCID 89668419, compound

HRID 1482204Notes

Reaction equation

HRID 1482204 reaction equation
Br[CH2:2][C:3]#[N:4].C(N(C(C)C)C(C)C)C.[C:14]([S:18][S:19][CH2:20][C@H:21]([NH:25][C:26](=[O:31])[CH2:27][CH2:28][CH:29]=[CH2:30])[C:22]([OH:24])=[O:23])([CH3:17])([CH3:16])[CH3:15].C(O)(=O)CCC=C.[Cl-].[NH4+]>CN(C)C=O>[C:14]([S:18][S:19][CH2:20][C@H:21]([NH:25][C:26](=[O:31])[CH2:27][CH2:28][CH:29]=[CH2:30])[C:22]([O:24][CH2:2][C:3]#[N:4])=[O:23])([CH3:17])([CH3:16])[CH3:15]

Participants

7

Reactant 5

HCID 11534BromoacetonitrileHCID 25517Ammonium ChlorideHCID 611384-Pentenoic acidHCID 81531DiisopropylethylamineHCID 89668385HCID 89668385, compound2×

Product 1

HCID 89668419HCID 89668419, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Bromoacetonitrile (0.957 ml, 13.74 mmol) and N-ethyl-N-isopropylpropan-2-amine (1.76 ml, 10.1 mmol) were added to a solution of the mixed crude product C (1.75 g, 8.70 mmol) of (R)-3-(tert-butyldisulfanyl)-2-(pent-4-enamido)propanoic acid (Compound 2k-C) and pent-4-enoic acid (1:0.9) in N,N-dimethylformamide (11 ml), and the mixture was stirred at room temperature for 50 minutes. A saturated aqueous ammonium chloride solution (6 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→50/50) to afford (R)-cyanomethyl 3-(tert-butyldisulfanyl)-2-(pent-4-enamido)propanoate (Compound 21-C) (940 mg, 62%).

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→50/50)

Sources & evidence

ORD record
ord-d91ddc668d254b94bfd65cba4be91222
Source dataset
uspto-grants-2016_08
Patent number
US09409952B2

Reaction notes

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