Hydrochloric Acid → HCID 58292767, compound

HRID 1798244Notes

Reaction equation

HRID 1798244 reaction equation
[OH:1][B:2]1[C:6]2[CH:7]=[C:8]([O:13][C:14]3[CH:19]=[N:18][CH:17]=[CH:16][N:15]=3)[CH:9]=[C:10]([O:11][CH3:12])[C:5]=2[CH:4]([CH2:20][C:21]([O:23]CC)=[O:22])[O:3]1.[OH-].[Li+].Cl>C1COCC1.O>[OH:1][B:2]1[C:6]2[CH:7]=[C:8]([O:13][C:14]3[CH:19]=[N:18][CH:17]=[CH:16][N:15]=3)[CH:9]=[C:10]([O:11][CH3:12])[C:5]=2[CH:4]([CH2:20][C:21]([OH:23])=[O:22])[O:3]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58292770HCID 58292770, compound

Product 1

HCID 58292767HCID 58292767, compoundYield 51.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-(1-hydroxy-4-methoxy-6-(pyrazin-2-yloxy)-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate (150 mg, 0.44 mmol) in THF (2 mL) was added an aqueous solution of lithium hydroxide (90 mg, 2.2 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 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 (71 mg, Y: 51.0%). 1H NMR (400 MHz, DMSO-d) δ 9.28 (s, 1H), 8.56 (s, 1H), 8.39-8.40 (d, J=2.4 Hz, 1H), 8.24 (s, 1H), 7.00-7.02 (d, J=10.8 Hz, 2H), 5.44-5.46 (m, 1H), 3.81 (s, 3H), 3.13-3.16 (m, 1H), 2.14-2.20 (m, 1H). MS (ESI) m/z=317 [M+H]+.

Workup

  1. extractionThe resulting mixture was extracted with ethyl acetate (15 mL×2)
  2. dry with materialwere dried over anhydrous Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-92864d43c1204db18912966b179c29e6
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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