Hydrochloric Acid → HCID 50923241, compound

HRID 1798250Notes

Reaction equation

HRID 1798250 reaction equation
[OH:1][B:2]1[C:6]2[CH:7]=[C:8]([O:15][C:16]3[CH:21]=[N:20][CH:19]=[CH:18][N:17]=3)[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]([O:15][C:16]3[CH:21]=[N:20][CH:19]=[CH:18][N:17]=3)[CH:9]=[C:10]([O:11][CH:12]([CH3:13])[CH3:14])[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 58292706HCID 58292706, compound

Product 1

HCID 50923241HCID 50923241, compoundYield 45.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of ethyl 2-(1-hydroxy-4-isopropoxy-6-(pyrazin-2-yloxy)-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate (96 mg, 0.26 mmol) in EtOH (4 mL) was added an aqueous solution of lithium hydroxide (21.8 mg, 0.52 mmol) in water (1 mL). The reaction mixture stirred at room temperature overnight and acidified with 1 N HCl to pH=4. The resulting mixture was extracted with EtOAc (15 mL) and combined organic layers were washed with water (10 mL) and brine (10 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 (41 mg. Yield: 45%). 1H NMR (400 MHz, DMSO-d6) δ 12.41-12.12 (m, 1H), 9.25 (s, 1H), 8.55 (d, J=0.8 Hz, 1H), 8.38 (d, J=2.8 Hz, 1H), 8.23 (t, J=1.2 Hz, 1H), 6.99 (s, 1H), 5.42 (m, 1H), 4.67 (m, 1H), 3.18 (m, 1H), 2.19 (m, 1H), 1.27 (m, 6H). MS (ESI) m/z=345 [M+H]+.

Workup

  1. extractionThe resulting mixture was extracted with EtOAc (15 mL)
  2. washwere washed with water (10 mL) and brine (10 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-932305639da3490f8d6c5a30a193b323
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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