Hydrochloric Acid → HCID 58292572, compound

HRID 1798094Notes

Reaction equation

HRID 1798094 reaction equation
C([O:3][C:4](=[O:19])[CH2:5][C@H:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([O:17][CH3:18])[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][CH3:18])[CH:14]=[C:15]([CH3:16])[C:7]=2[C@@H:6]([CH2:5][C:4]([OH:19])=[O:3])[O:10]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58292817HCID 58292817, compound

Product 1

HCID 58292572HCID 58292572, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (3R)-(1-hydroxy-6-methoxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid ethyl ester (0.68 g, 2.57 mmol) in THF (7 mL) was added a solution of LiOH (0.31 g, 12.87 mmol) in water (7 mL) at 0° C. The resulting mixture was stirred at room temperature for 3 hours then acidified to pH 2 using 6M hydrochloric acid and extracted with EtOAc. The organic extracts were washed with water, brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by silica gel flash column chromatography (0-5% MeOH in DCM) to give (3R)-(1-hydroxy-6-methoxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid as an off white solid (0.45 g, 74%). mp 48.2-50° C. 1HNMR (400 MHz, DMSO-d δ 9.10 (s, 1H), 7.02 (d, J=2.34 Hz, 1H), 6.83 (d, J=1.76 Hz, 1H), 5.42 (dd, J=9.67, 2.64 Hz, 1H), 3.73 (s, 3H), 3.01 (dd, J=15.38, 2.49 Hz, 1H), 2.24 (s, 3H), 2.03 (m, 1H). MS (ESI) m/z: 235 (M−1)−. HPLC purity: 98.31% (Maxplot), 97.78% (220 nm).

Workup

  1. extractionextracted with EtOAc
  2. washThe organic extracts were washed with water, brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel flash column chromatography (0-5% MeOH in DCM)

Sources & evidence

ORD record
ord-20fe2d82335643d3aa61b3179a6bf853
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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