Water → HCID 66976414, compound

HRID 1022801Notes

Reaction equation

HRID 1022801 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH:15]([CH2:16]O)[O:14][CH2:13][CH2:12][N:11]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[CH2:25]([N:27](CC)CC)C.CS(Cl)(=O)=O.O>C1COCC1>[C:25]([CH2:16][CH:15]1[O:14][CH2:13][CH2:12][N:11]([C:18]([O:20][C:21]([CH3:23])([CH3:24])[CH3:22])=[O:19])[CH2:10][CH:9]1[C:4]1[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=1)#[N:27]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 66975659HCID 66975659, compound

Product 1

HCID 66976414HCID 66976414, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl (6RS,7SR)-6-(3,4-dichlorophenyl)-7-(hydroxymethyl)-1,4-oxazepane-4-carboxylate (2.0 g) in THF (40 mL) were added triethylamine (2.22 mL) and methanesulfonyl chloride (0.82 mL) under ice-cooling, and the mixture was stirred at room temperature for 2 hr. To the reaction solution was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. To a solution of the obtained residue (1.6 g) in DMF (9.0 ml) was added sodium cyanide (345 mg), and the mixture was stirred at 80° C. for 2 days. The reaction solution was allowed to cool to room temperature, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with 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 (331 mg).

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. additionTo a solution of the obtained residue (1.6 g) in DMF (9.0 ml) was added sodium cyanide (345 mg)
  7. stirringthe mixture was stirred at 80° C. for 2 days
  8. temperatureto cool to room temperature
  9. additionwater was added
  10. extractionthe mixture was extracted with ethyl acetate
  11. washThe organic layer was washed with water and brine
  12. dry with materialdried over anhydrous magnesium sulfate
  13. customThe solvent was evaporated under reduced pressure
  14. customThe residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-be4b4309890f4595b1cd06fe4093a302
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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