Hydrochloric Acid → HCID 58292697, compound

HRID 1798228Notes

Reaction equation

HRID 1798228 reaction equation
C([O:3][C:4](=[O:26])[CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([O:17][C:18]3[C:23]([C:24]#N)=[N:22][CH:21]=[CH:20][N:19]=3)[CH:14]=[C:15]([CH3:16])[C:7]1=2)C.[OH-:27].[Na+].Cl.[OH2:30]>C1COCC1>[C:4]([CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([O:17][C:18]3[C:23]([C:24]([OH:30])=[O:27])=[N:22][CH:21]=[CH:20][N:19]=3)[CH:14]=[C:15]([CH3:16])[C:7]1=2)([OH:3])=[O:26]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 58292872HCID 58292872, compound

Product 1

HCID 58292697HCID 58292697, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [6-(3-cyano-pyrazin-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester (100 mg, 0.283 mmol) in THF (3 mL) was added NaOH (1N in H2O, 2.0 mL). The resulting solution was stirred at room temperature overnight. The mixture was diluted with H2O and acidified to pH 3 with 1N HCl at 0° C. The resulting mixture was extracted with ethyl acetate. The organic phase was separated, dried (Na2SO4), and concentrated. The crude mixture was purified by prep HPLC to give the title compound (150 mg, 82%) as a white solid. 1H NMR (CD3OD) δ 8.33 (d, 1H), 8.23 (d, 1H), 7.20 (d, 1H), 7.08 (d, 1H), 5.64 (dd, 1H), 3.15 (dd, 1H), 2.34 (s, 3H), 2.26 (dd, 1H). MS found: (M+H)+: 345.

Workup

  1. extractionThe resulting mixture was extracted with ethyl acetate
  2. customThe organic phase was separated
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe crude mixture was purified by prep HPLC

Sources & evidence

ORD record
ord-39fe3237595a45cba686531eeeb0db2b
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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