Hydrochloric Acid → HCID 58292680, compound

HRID 1798165Notes

Reaction equation

HRID 1798165 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[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)[CH:14]=[C:15]([CH3:16])[C:7]1=2)C.[Li+].[OH-].Cl>C1COCC1.O>[OH:11][B:9]1[C:8]2[CH:12]=[C:13]([O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=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 58292838HCID 58292838, compound

Product 1

HCID 58292680HCID 58292680, compoundYield 75.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [1-hydroxy-4-methyl-6-(pyridin-2-yloxy)-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester (75 mg, 0.23 mmol) in THF (4 mL) was added LiOH (20 mg, 0.48 mmol) in water (2 mL). The mixture was stirred at room temperature for 5 h and acidified by 1N HCl to pH 3. The mixture was concentrated and purified by HPLC affording the title compound (52 mg, 75%) as a white solid. 1H NMR (DMSO) δ 9.26 (m, 1H), 8.19 (s, 1H), 7.89 (m, 1H), 7.24 (s, 1H), 7.17 (m, 1H), 7.08 (m, 1H), 7.05 (m, 1H), 5.55 (d, 1H), 3.13 (d, 1H), 2.31 (s, 3H), 2.13 (m, 1H). MS found: (M+H)+=300.10.

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by HPLC

Sources & evidence

ORD record
ord-2f7f55d7c9814a0ab1b70eb25c3850b2
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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