Sodium Cyanide → HCID 66975209, compound

HRID 1022667Notes

Reaction equation

HRID 1022667 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[O:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11][CH:10]2[CH2:23]OS(C)(=O)=O)[CH:5]=[CH:6][C:7]=1[Cl:8].[C-:29]#[N:30].[Na+]>CN(C=O)C>[C:29]([CH2:23][CH:10]1[CH:9]([C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)[O:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:20])[CH3:21])=[O:17])[CH2:11]1)#[N:30]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 86663847HCID 86663847, compound

Product 1

HCID 66975209HCID 66975209, compoundYield 92.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of tert-butyl (6RS,7SR)-7-(3,4-dichlorophenyl)-6-{[(methylsulfonyl)oxy]methyl}-1,4-oxazepane-4-carboxylate (1.26 g) in DMF (10 mL) was added sodium cyanide (204 mg), and the mixture was stirred at 80° C. for 18 hr. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with ethyl acetate. The diluted solution was washed with distilled water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (990 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionthe residue was diluted with ethyl acetate
  3. washThe diluted solution was washed with distilled water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-269dd33d23424fe896852935e300142a
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

Loading…