Hydrogen chloride-ethyl acetate → HCID 67778466, compound

HRID 1026302Notes

Reaction equation

HRID 1026302 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[CH:8][C:9]3[C:13]([CH:14]=2)=[N:12][N:11]([C:15]2[CH:32]=[CH:31][C:18]([O:19][CH2:20][C@@H:21]([NH:23]C(=O)OC(C)(C)C)[CH3:22])=[CH:17][C:16]=2[F:33])[CH:10]=3)[CH2:3][CH2:2]1.Cl.C(OCC)(=O)C>>[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[CH:8][C:9]3[C:13]([CH:14]=2)=[N:12][N:11]([C:15]2[CH:32]=[CH:31][C:18]([O:19][CH2:20][C@@H:21]([NH2:23])[CH3:22])=[CH:17][C:16]=2[F:33])[CH:10]=3)[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 86666301HCID 86666301, compound

Product 1

HCID 67778466HCID 67778466, compoundYield 99.9%

Procedure

A mixture of tert-butyl [(1S)-2-{4-[6-(cyclopropylmethoxy)-2H-indazol-2-yl]-3-fluorophenoxy}-1-methylethyl]carbamate (544 mg) and 4M hydrogen chloride/ethyl acetate (5 mL) was stirred at room temperature for 1 hr. The reaction mixture was concentrated under reduced pressure, to the obtained residue was added saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted twice 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 to give the title compound as an orange oil (424 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, to the obtained residue
  2. additionwas added saturated aqueous sodium hydrogen carbonate solution
  3. extractionthe mixture was extracted twice with ethyl acetate
  4. washThe combined organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-693dcbf141744b76b5eb935d97c19edb
Source dataset
uspto-grants-2014_05
Patent number
US08729102B2

Reaction notes

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