Hydrochloric Acid → HCID 50923084, compound

HRID 1798030Notes

Reaction equation

HRID 1798030 reaction equation
C([O:3][C:4](=[O:19])[CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([OH:18])[CH:14]=[C:15]([CH2:16][CH3:17])[C:7]1=2)C.[Li+].[OH-].Cl>C1COCC1.O>[CH2:16]([C:15]1[C:7]2[CH:6]([CH2:5][C:4]([OH:19])=[O:3])[O:10][B:9]([OH:11])[C:8]=2[CH:12]=[C:13]([OH:18])[CH:14]=1)[CH3:17]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58292542HCID 58292542, compound

Product 1

HCID 50923084HCID 50923084, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (4-ethyl-1,6-dihydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid ethyl ester (0.19 g, 0.70 mmol) in THF (8 mL) and H2O (2 mL) was added LiOH (0.178 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 in vacuo and the residue purified by preparative HPLC to give (4-ethyl-1,6-dihydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid (0.080 g, 50%). 1H NMR (400 MHz, DMSO-d6δ 9.26 (s, 1H), 6.87 (s, 1H), 6.69 (s, 1H), 5.40 (m, 1H), 2.92 (m, 1H), 2.55 (m, 2H), 2.00 (m, 1H), 1.16 (m, 3H). MS (ESI) m/z: 235 [M−1]−. HPLC purity: 92.64% (220 nm), 95.63% (Maxplot).

Workup

  1. temperaturethen cooled to 0° C.
  2. concentrationThe mixture was concentrated in vacuo
  3. customthe residue purified by preparative HPLC

Sources & evidence

ORD record
ord-f886160c002041dd80dd5c7ac5b7aa4b
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

Loading…