Water → HCID 86663876, compound

HRID 1022792Notes

Reaction equation

HRID 1022792 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]2[C@@H:15](CO)[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].C(N([CH2:30][CH3:31])CC)C.[CH3:32][S:33](Cl)(=O)=O.[OH2:37]>C1COCC1>[C:30]([S:33][CH2:32][C@H:15]1[O:14][CH2:13][CH2:12][N:11]([C:18]([O:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[O:19])[CH2:10][C@H:9]1[C:4]1[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=1)(=[O:37])[CH3:31]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 66976480HCID 66976480, compound

Product 1

HCID 86663876HCID 86663876, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl (6R,7S)-6-(3,4-dichlorophenyl)-7-(hydroxymethyl)-1,4-oxazepane-4-carboxylate (2.15 g) in THF (45 ml) were added triethylamine (2.39 mL) and methanesulfonyl chloride (0.98 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. The residue (244 mg) was dissolved in acetonitrile (5 mL), cesium carbonate (184 mg) and thioacetic acid (0.04 mL) were added, and the mixture was stirred at room temperature overnight. 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. The residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (45 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. dissolutionThe residue (244 mg) was dissolved in acetonitrile (5 mL)
  7. additioncesium carbonate (184 mg) and thioacetic acid (0.04 mL) were added
  8. stirringthe mixture was stirred at room temperature overnight
  9. additionTo the reaction solution was added water
  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-5d32b7a6c0e148e29ba01318c0aa22ae
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

Loading…