Hydrochloric Acid → HCID 58292623, compound

HRID 1798110Notes

Reaction equation

HRID 1798110 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][CH:19]([CH3:21])[CH3:20])[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][CH:19]([CH3:21])[CH3:20])[CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58292803HCID 58292803, compound

Product 1

HCID 58292623HCID 58292623, compoundYield 18%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-(4-fluoro-1-hydroxy-6-isopropoxy-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate (148 mg, 0.50 mmol) in THF (2 mL) was added dropwise an solution of lithium hydroxide (102 mg, 2.5 mmol) in 3 mL of water at 0° C. The reaction mixture was stirred at room temperature for 1.5 h and then acidified to pH=2 using diluted hydrochloride acid. The reaction mixture was extracted with ethyl acetate (15 mL×2) and 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 (24 mg, Yield: 18%). 1H NMR (400 MHz, DMSO-d) δ 12.40 (s, 1H), 9.39 (s, 1H), 7.06-7.07 (d, J=2.0 Hz, 1H), 6.87-6.91 (m, 1H), 5.51-5.54 (m, 1H), 4.62-4.64 (m, 2H), 2.90-2.95 (m, 1H), 2.31-2.33 (m, 1H), 1.28 (s, 1H). MS (ESI) m/z=536 [2M]+.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate (15 mL×2)
  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-0f5f5d52a7b74904bcd54c304c82f1ea
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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