Hydrochloric Acid → HCID 58292601, compound

HRID 1798069Notes

Reaction equation

HRID 1798069 reaction equation
C([O:3][C:4](=[O:19])[CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([OH:18])[CH:14]=[C:15]([O:16][CH3:17])[C:7]1=2)C.[OH-].[Li+].Cl>C1COCC1.O>[OH:11][B:9]1[C:8]2[CH:12]=[C:13]([OH:18])[CH:14]=[C:15]([O:16][CH3:17])[C:7]=2[CH:6]([CH2:5][C:4]([OH:19])=[O:3])[O:10]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58292699HCID 58292699, compound

Product 1

HCID 58292601HCID 58292601, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl-2-(1,6-dihydroxy-4-methoxy-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate (133 mg, 0.50 mmol) in THF (2 mL) was added aqueous 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 hr and acidified to pH=2 using diluted hydrochloride acid. The resulting mixture was extracted with ethyl acetate (15 mL×2) and the combined organic layers were dried over anhydrous and concentrated in vacuo. The residue was purified by HPLC to give the title as a white solid (63 mg, Yield: 53%). 1H NMR (400 MHz, DMSO-d) δ 9.49 (s, 1H), 9.15 (s, 1H), 6.65 (s, 1H), 6.48 (s, 1H), 5.31-5.34 (m, 1H), 3.77 (s, 3H), 3.04-3.09 (m, 1H), 1.98-2.04 (m, 1H). MS (ESI) m/z=239 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-b50995fcc3844fecbc04c46930a58c80
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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