Hydrogen chloride-ethyl acetate → HCID 57341704, compound

HRID 1026222Notes

Reaction equation

HRID 1026222 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:33]=[CH:32][C:9]3[N:10]=[C:11]([C:13]4[N:18]=[CH:17][C:16]([O:19][CH2:20][C@@H:21]([NH:23]C(=O)OC(C)(C)C)[CH3:22])=[CH:15][C:14]=4[F:31])[O:12][C:8]=3[CH:7]=2)[CH2:3][CH2:2]1.Cl.[C:35](OCC)(=[O:37])[CH3:36]>C(OCC)(=O)C>[CH:1]1([CH2:4][O:5][C:6]2[CH:33]=[CH:32][C:9]3[N:10]=[C:11]([C:13]4[N:18]=[CH:17][C:16]([O:19][CH2:20][C@@H:21]([NH:23][C:35](=[O:37])[CH3:36])[CH3:22])=[CH:15][C:14]=4[F:31])[O:12][C:8]=3[CH:7]=2)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 86666269tert-butyl [(1S)-2-({6-[6-(cyclopropylmethoxy)-1,3-benzoxazol-2-yl]-5-fluoropyridin-3-yl}oxy)-1-methylethyl]carbamate

Product 1

HCID 57341704HCID 57341704, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of tert-butyl [(1S)-2-({6-[6-(cyclopropylmethoxy)-1,3-benzoxazol-2-yl]-5-fluoropyridin-3-yl}oxy)-1-methylethyl]carbamate (101 mg), 4M hydrogen chloride/ethyl acetate (1 mL) and ethyl acetate (1 mL) was stirred at room temperature for 2 hr. The solvent was evaporated under reduced pressure, and the residue was mixed with acetic anhydride (1 mL) and pyridine (1 mL), and the obtained mixture was stirred at room temperature for 1 hr. To the reaction mixture was added 1M hydrochloric acid, and the mixture was extracted with ethyl acetate. The combined organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate/methanol), and recrystallized (hexane/ethyl acetate) to give the title compound (53.1 mg).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionthe residue was mixed with acetic anhydride (1 mL) and pyridine (1 mL)
  3. stirringthe obtained mixture was stirred at room temperature for 1 hr
  4. additionTo the reaction mixture was added 1M hydrochloric acid
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe combined organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate/methanol)
  10. customrecrystallized (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-81342b3bb7454ea59b964f6c82cbfd78
Source dataset
uspto-grants-2014_05
Patent number
US08729102B2

Reaction notes

Loading…