HCID 66975176, compound → HCID 66975848, compound

HRID 1022702Notes

Reaction equation

HRID 1022702 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][CH2:9][C@H:10]1[C@H:16]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=2)[O:15][CH2:14][CH2:13][N:12]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:11]1.[Cu](C#N)[C:33]#[N:34]>CN(C=O)C>[C:33]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][CH2:9][C@H:10]1[C@H:16]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=2)[O:15][CH2:14][CH2:13][N:12]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:11]1)#[N:34]

Participants

4

Reactant 2

HCID 66975176HCID 66975176, compoundHCID 178418260HCID 178418260, compound

Product 1

HCID 66975848HCID 66975848, compoundYield 38.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

To a solution (7.8 mL) of tert-butyl (6R,7R)-6-{[(2-bromophenyl)sulfanyl]methyl}-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate (424 mg) in DMF was added copper cyanide (139 mg), and the mixture was stirred under an argon atmosphere at 150° C. overnight. The reaction mixture was filtered through celite, distilled water was added, and the mixture was extracted with ethyl acetate. The extract was washed with distilled water and brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (146 mg).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. distillationdistilled water
  3. additionwas added
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with distilled water and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-cf9a3ba54e524bf2ad628d5775e70279
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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