Hydrochloric Acid → HCID 58292812, compound

HRID 1798226Notes

Reaction equation

HRID 1798226 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:25])=[N:22][CH:21]=[CH:20][N:19]=3)[CH:14]=[C:15]([CH3:16])[C:7]1=2)C.[Li+].[OH-].Cl>C1COCC1.O>[C:24]([C:23]1[C:18]([O:17][C:13]2[CH:14]=[C:15]([CH3:16])[C:7]3[CH:6]([CH2:5][C:4]([OH:26])=[O:3])[O:10][B:9]([OH:11])[C:8]=3[CH:12]=2)=[N:19][CH:20]=[CH:21][N:22]=1)#[N:25]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58292872HCID 58292872, compound

Product 1

HCID 58292812HCID 58292812, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

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 (200 mg, 0.566 mmol) in THF (5 mL) and H2O (2 mL) was added LiOH (0.120 g, 2.83 mmol). The resulting solution was stirred at 0° C. for 2 hrs. 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 title compound was obtained (150 mg, 82%) as a white solid. 1H NMR (CD3OD) δ8.42 (d, 1H), 8.38 (d, 1H), 7.32 (d, 1H), 7.18 (d, 1H), 5.65 (dd, 1H), 3.20 (dd, 1H), 2.41 (s, 3H), 2.36 (dd, 1H). MS found: (M+H)+: 326.

Workup

  1. extractionThe resulting mixture was extracted with ethyl acetate
  2. customThe organic phase was separated
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f7628e83c979428cbd15442dd2c1e64f
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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