Hydrochloric Acid → HCID 58292717, compound

HRID 1798214Notes

Reaction equation

HRID 1798214 reaction equation
C([O:3][C:4](=[O:25])[CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([O:18][C:19]3[CH:24]=[N:23][CH:22]=[CH:21][N:20]=3)[CH:14]=[C:15]([CH2:16][CH3:17])[C:7]1=2)C.[Li+].[OH-].Cl>C1COCC1.O>[CH2:16]([C:15]1[C:7]2[CH:6]([CH2:5][C:4]([OH:25])=[O:3])[O:10][B:9]([OH:11])[C:8]=2[CH:12]=[C:13]([O:18][C:19]2[CH:24]=[N:23][CH:22]=[CH:21][N:20]=2)[CH:14]=1)[CH3:17]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58292775HCID 58292775, compound

Product 1

HCID 58292717HCID 58292717, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [4-ethyl-1-hydroxy-6-(pyrazin-2-yloxy)-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester (0.11 g, 0.32 mmol) in THF (4 mL) and H2O (2 mL) was added LiOH (0.040 g) at 0° C. The resulting mixture was stirred at room temperature for 2 hours then cooled to 0° C. and acidified to pH 3 with 6N HCl. The mixture was concentrated in vacuo and the residue purified by silica gel flash column chromatography to give [4-ethyl-1-hydroxy-6-(pyrazin-2-yloxy)-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid (0.080 g, 80%). 1H NMR (400 MHz, DMSO-d6) δ 12.39 (s, 1H), 9.20 (s, 1H), 8.56 (s, 1H), 8.38 (s, 1H), 8.22 (s, 1H), 7.27 (s, 1H), 7.16 (s, 1H), 5.56 (s, 1H), 3.05 (M, 1H), 2.65 (m, 2H), 2.19 (M, 1H), 1.20 (M, 3H). MS (ES) m/z: 315 (M+1)+. HPLC purity: 99.19% (220 nm), 98.31% (Maxplot).

Workup

  1. temperaturethen cooled to 0° C.
  2. concentrationThe mixture was concentrated in vacuo
  3. customthe residue purified by silica gel flash column chromatography

Sources & evidence

ORD record
ord-91b5611dd71e437e805fa77f515a2aa1
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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