Hydrochloric Acid → HCID 58292728, compound

HRID 1798049Notes

Reaction equation

HRID 1798049 reaction equation
C([O:3][C:4](=[O:18])[CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([OH:17])[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:18])=[O:3])[O:10][B:9]([OH:11])[C:8]=2[CH:12]=[C:13]([OH:17])[CH:14]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58292615HCID 58292615, compound

Product 1

HCID 58292728HCID 58292728, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl-2-(4-fluoro-1,6-dihydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate (127 mg, 0.50 mmol) in THF (2 mL) was added dropwise a solution of lithium hydroxide (102 mg, 2.5 mmol) in water (3 mL) at 0° C. The mixture was stirred at room temperature for 1.5 h and after cooling to 0° C., acidified to pH=2 by addition of diluted hydrochloride acid, extracted with ethyl acetate (2×15 mL). The combined extracts were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by HPLC to give the title compound as a white solid (52 mg, Yield: 46%). 1H NMR (400 MHz, DMSO-d) δ 12.12 (s, 1H), 9.91 (s, 1H), 9.37 (s, 1H), 6.94-6.94 (d, J=1.6 Hz, 1H), 6.65-6.68 (m, 1H), 5.46-5.49 (m, 1H), 2.88-2.93 (m, 1H), 2.23-2.29 (m, 1H). MS (ESI) m/z=455 [2M+H]+.

Workup

  1. temperatureafter cooling to 0° C.
  2. extractionextracted with ethyl acetate (2×15 mL)
  3. dry with materialThe combined extracts were dried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-b100494eac994e228613194d9b1f749e
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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