Hydrochloric Acid → HCID 58292705, compound

HRID 1798096Notes

Reaction equation

HRID 1798096 reaction equation
[F:1][C:2]1[C:10]2[CH:9]([CH2:11][C:12]([O:14]CC)=[O:13])[O:8][B:7]([OH:17])[C:6]=2[CH:5]=[C:4]([O:18][CH3:19])[CH:3]=1.[OH-].[Li+].Cl>C1COCC1.O>[F:1][C:2]1[C:10]2[CH:9]([CH2:11][C:12]([OH:14])=[O:13])[O:8][B:7]([OH:17])[C:6]=2[CH:5]=[C:4]([O:18][CH3:19])[CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58292860HCID 58292860, compound

Product 1

HCID 58292705HCID 58292705, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-(4-fluoro-1-hydroxy-6-methoxy-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate (134 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 with diluted hydrochloride acid. 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 (43 mg, Yield: 36%). 1H NMR (400 MHz, DMSO-d) δ 12.20 (s, 1H), 9.45 (s, 1H), 7.09-7.09 (d, J=1.6 Hz, 1H), 6.91-6.95 (m, 1H), 5.51-5.55 (m, 1H), 3.80 (s, 3H), 2.91-2.97 (m, 1H), 2.27-2.33 (m, 1H). MS (ESI) m/z=481 [2M+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-116f511faa8d4f75bc3dd38102782a60
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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