Hydrogen chloride-ethyl acetate → HCID 66976532, compound

HRID 1022609Notes

Reaction equation

HRID 1022609 reaction equation
[C:1]([NH:4][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)(=[O:3])[CH3:2].C(OCC)(=O)C.Cl>C(O)C>[Cl:20][C:15]1[CH:14]=[C:13]([C@@H:12]2[O:11][CH2:10][CH2:9][NH:8][CH2:7][C@H:6]2[CH2:5][NH:4][C:1](=[O:3])[CH3:2])[CH:18]=[CH:17][C:16]=1[Cl:19]

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 66976309HCID 66976309, compound

Product 1

HCID 66976532HCID 66976532, compoundYield 60.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of tert-butyl (6R,7R)-6-[(acetylamino)methyl]-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate (160 mg) in ethanol (0.5 mL) was added 4.0 M hydrogen chloride-ethyl acetate solution (3 mL), and the mixture was stirred at room temperature for 1.5 hr. The solvent was evaporated under reduced pressure. To the residue was added 1 N aqueous sodium hydroxide solution, and the mixture was extracted twice with ethyl acetate. The combined organic layers were washed with brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was dissolved in ethanol, and a solution of fumaric acid (39.3 mg) in ethanol was added. The solvent was evaporated under reduced pressure. The obtained crystals were recrystallized from ethanol-ethyl acetate to give the title compound (73.5 mg) as colorless crystals.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionTo the residue was added 1 N aqueous sodium hydroxide solution
  3. extractionthe mixture was extracted twice with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. dissolutionThe residue was dissolved in ethanol
  8. additiona solution of fumaric acid (39.3 mg) in ethanol was added
  9. customThe solvent was evaporated under reduced pressure
  10. customThe obtained crystals were recrystallized from ethanol-ethyl acetate

Sources & evidence

ORD record
ord-23f8f66375d74b9f88b70b8bd177ae1a
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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