Hydrochloric Acid → HCID 58292603, compound

HRID 1798324Notes

Reaction equation

HRID 1798324 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[S:22][N:21]=[C:20]([Cl:23])[N:19]=3)[CH:14]=[C:15]([CH3:16])[C:7]1=2)C.[Li+].[OH-].Cl>C1COCC1.O>[Cl:23][C:20]1[N:19]=[C:18]([O:17][C:13]2[CH:14]=[C:15]([CH3:16])[C:7]3[CH:6]([CH2:5][C:4]([OH:24])=[O:3])[O:10][B:9]([OH:11])[C:8]=3[CH:12]=2)[S:22][N:21]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58292560HCID 58292560, compound

Product 1

HCID 58292603HCID 58292603, compoundYield 18%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [6-(3-chloro-[1,2,4]thiadiazol-5-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester (135 mg, 0.502 mmol) in THF (5 mL) and H2O (2 mL) was added LiOH (0.105 g, 2.50 mmol). The resulting solution was stirred at room temperature 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 crude mixture was purified by prep HPLC to give title compound (20 mg, 18%) as a white solid. 1H NMR (CD3OD) δ7.42 (d, 1H), 7.29 (d, 1H), 5.66 (dd, 1H), 3.20 (dd, 1H), 2.40 (s, 3H), 2.36 (dd, 1H). MS found: (M+H)+: 341.

Workup

  1. extractionThe resulting mixture was extracted with ethyl acetate
  2. customThe organic phase was separated
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe crude mixture was purified by prep HPLC

Sources & evidence

ORD record
ord-fe3dc7d168db44aaae9f7154b1ae62ab
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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