Hydrochloric Acid → HCID 58292575, compound

HRID 1798247Notes

Reaction equation

HRID 1798247 reaction equation
[OH:1][B:2]1[C:6]2[CH:7]=[C:8]([O:12][C:13]3[CH:18]=[N:17][CH:16]=[CH:15][N:14]=3)[CH:9]=[C:10]([OH:11])[C:5]=2[CH:4]([CH2:19][C:20]([O:22]CC)=[O:21])[O:3]1.[OH-].[Li+].Cl>CCO.O>[OH:1][B:2]1[C:6]2[CH:7]=[C:8]([O:12][C:13]3[CH:18]=[N:17][CH:16]=[CH:15][N:14]=3)[CH:9]=[C:10]([OH:11])[C:5]=2[CH:4]([CH2:19][C:20]([OH:22])=[O:21])[O:3]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58292578HCID 58292578, compound

Product 1

HCID 58292575HCID 58292575, compoundYield 18.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of ethyl 2-(1,4-dihydroxy-6-(pyrazin-2-yloxy)-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate (100 mg, 0.31 mmol) in EtOH (5 ml) was added an aqueous solution of lithium hydroxide (26.1 mg, 0.62 mmol) in water (1 mL). The reaction mixture was stirred at room temperature overnight and acidified with 1 N HCl to pH=3. The resulting mixture was extracted with EtOAc (20 mL) and combined organic layers were washed with water (15 mL) and brine (15 mL), dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by prep HPLC to give the title compound as a white powder (17 mg, yield: 18%). 1H NMR (400 MHz, DMSO-d6) δ 12.31 (s, 1H), 10.13 (s, 1H), 9.19 (s, 1H), 8.54 (s, 1H), 8.38 (d, J=2.8 Hz, 1H), 8.24 (d, J=1.2 Hz, 1H), 6.90 (d, J=1.6 Hz, 1H), 5.44 (m, 1H), 3.22 (m, 1H), 2.18-2.11 (m, 1H). MS (ESI) m/z=303 [M+H]+.

Workup

  1. extractionThe resulting mixture was extracted with EtOAc (20 mL)
  2. washwere washed with water (15 mL) and brine (15 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by prep HPLC

Sources & evidence

ORD record
ord-b71e425868d745b78163692b437493e3
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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