Hydrochloric Acid → HCID 58292702, compound

HRID 1798217Notes

Reaction equation

HRID 1798217 reaction equation
C([O:3][C:4](=[O:24])[CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([O:17][C:18]3[CH:23]=[N:22][CH:21]=[CH:20][N:19]=3)[CH:14]=[C:15]([F:16])[C:7]1=2)C.[OH-].[Li+].Cl>C1COCC1.O>[F:16][C:15]1[C:7]2[CH:6]([CH2:5][C:4]([OH:24])=[O:3])[O:10][B:9]([OH:11])[C:8]=2[CH:12]=[C:13]([O:17][C:18]2[CH:23]=[N:22][CH:21]=[CH:20][N:19]=2)[CH:14]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58292620HCID 58292620, compound

Product 1

HCID 58292702HCID 58292702, compoundYield 13.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl-2-(4-fluoro-1-hydroxy-6-(pyrazin-2-yloxy)-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate (166 mg, 0.50 mmol) in THF (2 mL) was added dropwise an aqueous solution of lithium hydroxide (102 mg, 2.5 mmol) in water (3 mL) at 0° C. The reaction mixture was stirred at room temperature for 1.5 h and acidified to pH=2 at 0° C. with a diluted HCl solution. The resulting mixture was extracted with ethyl acetate (2×15 mL), the combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by HPLC to give the title compound as a white solid (21 mg, Yield: 13.8%). 1H NMR (400 MHz, DMSO-d) δ 12.50 (s, 1H), 9.50 (s, 1H), 8.61-8.62 (d, J=2.8 Hz, 1H), 8.42-8.43 (d, J=2.8 Hz, 1H), 8.24-8.25 (m, 1H), 7.31-7.33 (m, 1H), 5.61-5.64 (m, 1H), 2.97-3.02 (m, 1H), 2.37-2.43 (m, 1H). MS (ESI) m/z=305 [M+H]+.

Workup

  1. extractionThe resulting mixture was extracted with ethyl acetate (2×15 mL)
  2. dry with materialthe combined organic layers were dried over anhydrous Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-9b7feeca1e824244aaf9b27d8ed57540
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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