Hydrochloric Acid → HCID 58292619, compound

HRID 1798041Notes

Reaction equation

HRID 1798041 reaction equation
C[O:2][C:3](=[O:18])[CH2:4][CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([OH:17])[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]([OH:17])[CH:14]=[C:15]([CH3:16])[C:7]=2[CH:6]([CH2:5][CH2:4][C:3]([OH:18])=[O:2])[O:10]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58292751HCID 58292751, compound

Product 1

HCID 58292619HCID 58292619, compoundYield 61.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(1,6-dihydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)propionic acid methyl ester (0.190 g, 0.76 mmol) in THF (4 mL) and H2O (2 mL) was added LiOH (0.146 g, 6.08 mmol) 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 and purified by silica gel flash column chromatography to give 3-(1,6-dihydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)propionic acid (0.110 g, 61%). 1H NMR (400 MHz, DMSO-d6) δ 9.20 (s, 1H), 9.00 (s, 1H), 6.88 (s, 1H), 6.66 (s, 1H), 2.30-2.10 (m, 6H), 1.50 (m, 1H). MS (ESI) m/z: 235 [M−1]−. HPLC purity: 99.06% (220 nm), 98.87% (Maxplot).

Workup

  1. temperaturethen cooled to 0° C.
  2. concentrationThe mixture was concentrated
  3. custompurified by silica gel flash column chromatography

Sources & evidence

ORD record
ord-ab4f89df907e468e88967ad27f323e6d
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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