Sodium Hydroxide → HCID 118513287, compound

HRID 1478816Notes

Reaction equation

HRID 1478816 reaction equation
[F:1][C:2]([F:24])([F:23])[O:3][C:4]1[CH:5]=[CH:6][C:7]2[N:13]3[N:14]=[N:15][C:16]([C:17]([O:19]CC)=[O:18])=[C:12]3[CH2:11][CH2:10][CH2:9][C:8]=2[CH:22]=1.[OH-].[Na+]>C1COCC1.CO>[F:24][C:2]([F:1])([F:23])[O:3][C:4]1[CH:5]=[CH:6][C:7]2[N:13]3[N:14]=[N:15][C:16]([C:17]([OH:19])=[O:18])=[C:12]3[CH2:11][CH2:10][CH2:9][C:8]=2[CH:22]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 118513296HCID 118513296, compound

Product 1

HCID 118513287HCID 118513287, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 8-(trifluoromethoxy)-5,6-dihydro-4H-benzo[f][1,2,3]triazolo[1,5-a]azepine-3-carboxylate (384 mg, 1.125 mmol) in THF (5 mL) and methanol (3 mL) was added 2M NaOH (aq) (2.81 mL, 5.63 mmol) and the mixture was stirred at RT for 45 mins. The resulting mixture was concentrated under reduced pressure to give a residue that was partitioned between EtOAc and water. The layers were separated and the aqueous layer was washed with EtOAc. The organic portions were discarded and the aqueous layer was treated with 2M HCl (aq) until acidic. The resulting solution was extracted with EtOAc and the organic extracts were dried over MgSO4, filtered and concentrated under reduced pressure to give the title compound as a yellow solid.

Workup

  1. concentrationThe resulting mixture was concentrated under reduced pressure
  2. customto give a residue that
  3. customwas partitioned between EtOAc and water
  4. customThe layers were separated
  5. washthe aqueous layer was washed with EtOAc
  6. additionthe aqueous layer was treated with 2M HCl (aq) until acidic
  7. extractionThe resulting solution was extracted with EtOAc
  8. dry with materialthe organic extracts were dried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5b3aa81905a348c58cdb48f4f46ca835
Source dataset
uspto-grants-2016_08
Patent number
US09403833B2

Reaction notes

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