Hydrochloric Acid → HCID 58292615, compound

HRID 1798048Notes

Reaction equation

HRID 1798048 reaction equation
[CH2:1]([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]C3CCCCO3)[CH:14]=[C:15]([F:16])[C:7]1=2)[CH3:2].Cl>C1COCC1>[CH2:1]([O:3][C:4](=[O:24])[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)[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67252001HCID 67252001, compound

Product 1

HCID 58292615HCID 58292615, compoundYield 70.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of ethyl-2-(4-fluoro-1-hydroxy-6-(tetrahydro-2H-pyran-2-yloxy)-1,3-dihydro benzo[c][1,2]oxaborol-3-yl)acetate (0.34 g, 1.0 mmol) in THF (10 mL) was added dropwise concentrated hydrochloride acid (0.2 mL) at 0° C. The reaction mixture was stirred at 0° C. for 1 h and quenched by addition of sat. aqueous NaHCO3 (20 mL). The resulting mixture was extracted with EtOAc(2×30 mL). The combined extracts were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography on silica gel (EtOAc/PE=1/4) to give the title compound as a light yellow solid (180 mg, Yield: 70.9%). 1H NMR (400 MHz, DMSO-d) δ 9.93 (s, 1H), 9.40 (s, 1H), 6.94-6.94 (d, J=1.6 Hz, 1H), 6.65-6.68 (m, 1H), 5.49-5.52 (m, 1H), 4.00-4.08 (m, 2H), 2.94-2.99 (m, 1H), 2.38-2.44 (m, 1H), 1.13-1.20 (m, 3H). MS (ESI) m/z=255 [M+H]+.

Workup

  1. customquenched by addition of sat. aqueous NaHCO3 (20 mL)
  2. extractionThe resulting mixture was extracted with EtOAc(2×30 mL)
  3. dry with materialThe combined extracts were dried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography on silica gel (EtOAc/PE=1/4)

Sources & evidence

ORD record
ord-1019a338f9ab417ab0e58c22cd4b5519
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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