Hydrochloric Acid → HCID 58292754, compound

HRID 1798090Notes

Reaction equation

HRID 1798090 reaction equation
[OH:1][B:2]1[C:6]2[CH:7]=[C:8]([O:15]C3CCCCO3)[CH:9]=[C:10]([O:11][CH:12]([CH3:14])[CH3:13])[C:5]=2[CH:4]([CH2:22][C:23]([O:25]CC)=[O:24])[O:3]1.[OH-].[Li+].Cl>CCO.O>[OH:1][B:2]1[C:6]2[CH:7]=[C:8]([OH:15])[CH:9]=[C:10]([O:11][CH:12]([CH3:14])[CH3:13])[C:5]=2[CH:4]([CH2:22][C:23]([OH:25])=[O:24])[O:3]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58292829HCID 58292829, compound

Product 1

HCID 58292754HCID 58292754, compoundYield 51.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of ethyl 2-(1-hydroxy-4-isopropoxy-6-(tetrahydro-2H-pyran-2-yloxy)-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate (110 mg, 0.29 mmol) in EtOH (4 mL) was added an aqueous solution of lithium hydroxide (25.2 mg, 0.60 mmol) in water (1 mL). The reaction mixture was stirred at room temperature for 30 min and acidified with 1N HCl to pH=4. The resulting mixture was extracted with EtOAc (2×20 mL). The combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by prep HPLC to give the title compound as a white powder (40 mg. Yield: 51.8%). 1H NMR (400 MHz, CDCl3) δ12.2 (s, 1H), 9.38 (s, 1H), 9.08 (s, 1H), 6.64 (3, 1H), 6.46 (s, 1H), 5.29-5.32 (m, 1H), 3.55 (m, 2H), 3.06-3.10 (m, 1H), 2.00-2.02 (m, 1H), 1.29-1.33 (m, 3H). MS (ESI) m/z=267 [M+H]+.

Workup

  1. extractionThe resulting mixture was extracted with EtOAc (2×20 mL)
  2. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by prep HPLC

Sources & evidence

ORD record
ord-8b9a94bc8fd14410a8b3cfd75d916399
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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