Hydrochloric Acid → HCID 50925302, compound

HRID 1798327Notes

Reaction equation

HRID 1798327 reaction equation
C([O:3][C:4](=[O:23])[CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([O:17][C:18]3[S:22][N: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[S:22][N:21]=[CH:20][N:19]=3)[CH:14]=[C:15]([CH3:16])[C:7]=2[CH:6]([CH2:5][C:4]([OH:23])=[O:3])[O:10]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58292614HCID 58292614, compound

Product 1

HCID 50925302HCID 50925302, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [1-hydroxy-4-methyl-6-([1,2,4]thiadiazol-5-yloxy)-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester (100 mg, 0.30 mmol) in THF (2.5 mL) and H2O (1 mL) was added LiOH (0.063 g, 1.50 mmol) at 0° C. The resulting solution was stirred at room temperature for 20 minutes. The mixture was diluted with H2O and acidified to pH 3 with 1N HCl at 0° C. The resulting mixture was purified by prep HPLC to give the title compound (37 mg, 45%) as a white solid. 1H NMR (CD3OD) δ7.06 (d, 1H), 6.84 (d, 1H), 5.44 (dd, 1H), 3.04 (dd, 1H), 2.30 (s, 3H), 2.18 (dd, 1H). MS found: (M+H)+: 307.

Workup

  1. customThe resulting mixture was purified by prep HPLC

Sources & evidence

ORD record
ord-a2ba9673340a4f38831b3558133368d1
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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