Hydrochloric Acid → HCID 58292679, compound

HRID 1798273Notes

Reaction equation

HRID 1798273 reaction equation
C([O:3][C:4](=[O:24])[CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([O:17][C:18]3[N:19]=[N:20][CH:21]=[CH:22][CH:23]=3)[CH:14]=[C:15]([CH3:16])[C:7]1=2)C.[Li+].[OH-].Cl>C1COCC1.O.O>[OH:11][B:9]1[C:8]2[CH:12]=[C:13]([O:17][C:18]3[N:19]=[N:20][CH:21]=[CH:22][CH:23]=3)[CH:14]=[C:15]([CH3:16])[C:7]=2[CH:6]([CH2:5][C:4]([OH:24])=[O:3])[O:10]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58292550HCID 58292550, compound

Product 1

HCID 58292679HCID 58292679, compoundYield 47.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of [1-hydroxy-4-methyl-6-(pyridazin-3-yloxy)-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester (0.35 g, 1.06 mmol) in THF:H2O (1:1, 6 mL) at 0° C. was added a solution of LiOH (0.076 g, 3.2 mmol) in water (1 mL). The solution was allowed to warm to room temperature over 3 hours then acidified to pH 2 with 1N HCl and extracted with EtOAc (2×10 mL). The organic extracts were washed with water (10 mL), dried and concentrated in vacuo. The residue was purified by silica gel flash column chromatography (DCM:MeOH 90:10) to give [1-hydroxy-4-methyl-6-(pyridazin-3-yloxy)-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid (0.15 g, 47%). 1H NMR (400 MHz, DMSO): δ 9.23 (s, 1H), 9.01 (dd, J=1.2, 4.4 Hz, 1H), 7.79-7.76 (m, 1H), 7.47 (dd, J=1.2, 9.2 Hz, 1H), 7.28 (d, J=2.0 Hz, 1H), 7.14 (d, J=2.0 Hz, 1H), 5.54 (dd, J=2.4 Hz, 1H), 3.10 (dd, J=2.4, 15.6 Hz, 1H), 2.32 (s, 3H), 2.19-2.12 (m, 1H). MS (ESI) m/z=299 [M−H]−.

Workup

  1. extractionextracted with EtOAc (2×10 mL)
  2. washThe organic extracts were washed with water (10 mL)
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel flash column chromatography (DCM:MeOH 90:10)

Sources & evidence

ORD record
ord-935f69a9c3da4e1ea47ffe252ddc671c
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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