Hydrochloric Acid → HCID 58292668, compound

HRID 1798102Notes

Reaction equation

HRID 1798102 reaction equation
C[O:2][C:3](=[O:19])[CH2:4][CH2:5][CH: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.[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[CH:6]([CH2:5][CH2:4][C:3]([OH:19])=[O:2])[O:10]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58292546HCID 58292546, compound

Product 1

HCID 58292668HCID 58292668, compoundYield 93.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(1-hydroxy-6-methoxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-propionic acid methyl ester (0.160 g, 0.60 mmol) in THF (4 mL) and H2O (2 mL) was added LiOH (0.116 g) at 0° C. The resulting mixture was stirred at room temperature for 2 hours then cooled to 0° C. and acidified to pH 3 with 6N HCl. The mixture was concentrated to approximately half its volume and the precipitated solid was filtered, washed with water and dried to give 3-(1-hydroxy-6-methoxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-propionic acid (0.140 g, 93%). 1H NMR (400 MHz, DMSO-d6) δ 9.06 (s, 1H), 7.02 (d, J=2 Hz, 1H), 6.81 (s, 1H), 5.12 (m, 1H), 3.72 (s, 3H), 2.30-2.20 (m, 5H), 2.10 (m, 1H), 1.50 (m, 1H). MS (ES) m/z: 249 (M−1)−. HPLC purity: 97.16% (220 nm), 96.94% (Maxplot).

Workup

  1. temperaturethen cooled to 0° C.
  2. concentrationThe mixture was concentrated to approximately half its volume
  3. filtrationthe precipitated solid was filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-c49d8b95463541bb853b8e956655a7e1
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

Loading…