Acetone → HCID 178434042, compound

HRID 1022713Notes

Reaction equation

HRID 1022713 reaction equation
[CH3:1]I.[NH2:3][C:4](=S)[CH2:5][C@H:6]1[C@H:12]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=2)[O:11][CH2:10][CH2:9][N:8](C(OC(C)(C)C)=O)[CH2:7]1.[C:29](=[O:32])([O-])[O-:30].[K+].[K+].[C:35]([NH:38][NH2:39])(=O)[CH3:36].C(=O)([O-])O.[Na+].[CH3:45][C:46]([CH3:48])=O>>[Cl:20][C:15]1[CH:14]=[C:13]([C@@H:12]2[O:11][CH2:10][CH2:9][N:8]([C:29]([O:30][C:46]([CH3:48])([CH3:1])[CH3:45])=[O:32])[CH2:7][C@H:6]2[CH2:5][C:4]2[NH:3][C:35]([CH3:36])=[N:38][N:39]=2)[CH:18]=[CH:17][C:16]=1[Cl:19]

Participants

7

Reactant 6

HCID 180AcetoneHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 14039AcetohydrazideHCID 516892Sodium BicarbonateHCID 86663871tert-butyl (6R,7R)-6-(2-amino-2-thioxoethyl)-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate

Product 1

HCID 178434042HCID 178434042, compoundYield 79%

Procedure

Methyl iodide (0.214 mL, 3.43 mmol) was added to a suspension of tert-butyl (6R,7R)-6-(2-amino-2-thioxoethyl)-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate (288 mg, 0.69 mmol) and potassium carbonate (142 mg, 1.03 mmol) in acetone (5 mL) at room temperature. The reaction mixture was stirred at room temperature for 4 hr, and concentrated under reduced pressure. To the residue was added aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was dissolved in toluene (5 ml), acetohydrazide (61.1 mg, 0.82 mmol) was added, and the mixture was stirred at 120° C. overnight while using a Dean-Stark trap. To the reaction mixture was added aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (241 mg, 0.545 mmol, 79%).

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionTo the residue was added aqueous sodium hydrogen carbonate solution
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. dissolutionThe residue was dissolved in toluene (5 ml)
  8. stirringthe mixture was stirred at 120° C. overnight
  9. extractionthe mixture was extracted with ethyl acetate
  10. washThe extract was washed with brine
  11. dry with materialdried over anhydrous sodium sulfate
  12. customThe solvent was evaporated under reduced pressure
  13. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-0dc2c02fac124c96bbb19acd3b653633
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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