Hydrochloric Acid → HCID 58292766, compound

HRID 1798137Notes

Reaction equation

HRID 1798137 reaction equation
[OH:1][B:2]1[C:6]2[CH:7]=[C:8]([O:12][S:13]([CH3:16])(=[O:15])=[O:14])[CH:9]=[C:10]([CH3:11])[C:5]=2[CH:4]([CH2:17][C:18]([O-:20])=[O:19])[O:3]1.[Li+].[OH-].Cl>CCO>[OH:1][B:2]1[C:6]2[CH:7]=[C:8]([O:12][S:13]([CH3:16])(=[O:15])=[O:14])[CH:9]=[C:10]([CH3:11])[C:5]=2[CH:4]([CH2:17][C:18]([OH:20])=[O:19])[O:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 86653976HCID 86653976, compound

Product 1

HCID 58292766HCID 58292766, compoundYield 17.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-(1-hydroxy-4-methyl-6-(methylsulfonyloxy)-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate in EtOH (10 mL) was added an aqueous solution of LiOH (3 mL, 10% aq.). The reaction mixture was stirred at 0° C. for 3 h. The reaction mixture was acidified with 1N HCl to pH=2 and extracted with EtOAc (2×20 mL). The combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by prep HPLC to give the title compound as an off-white powder (64 mg, yield: 17.2%, two steps). 1H NMR (400 MHz, DMSO) δ 12.36 (s, 1H), 9.36 (s, 1H), 7.46 (d, J=2.0 Hz, 1H), 7.26 (d, J=2.0 Hz, 1H), 5.53-5.55 (m, 1H), 3.38 (s, 3H), 3.06-3.10 (m, 1H), 2.34 (s, 3H), 2.14-2.20 (m, 3H); MS (ESI) m/z=323 [M+Na]+.

Workup

  1. extractionextracted with EtOAc (2×20 mL)
  2. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by prep HPLC

Sources & evidence

ORD record
ord-15f63efa61e247db9112fa0d4d8e1870
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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