Hydrochloric Acid → (1,6-Dihydroxy-4-methoxymethyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid

HRID 1798063Notes

Reaction equation

HRID 1798063 reaction equation
C([O:3][C:4](=[O:20])[CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([OH:19])[CH:14]=[C:15]([CH2:16][O:17][CH3:18])[C:7]1=2)C.[Li+].[OH-].Cl>C1COCC1.O>[OH:11][B:9]1[C:8]2[CH:12]=[C:13]([OH:19])[CH:14]=[C:15]([CH2:16][O:17][CH3:18])[C:7]=2[CH:6]([CH2:5][C:4]([OH:20])=[O:3])[O:10]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58292640(1,6-Dihydroxy-4-methoxymethyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid ethyl ester

Product 1

HCID 58292758(1,6-Dihydroxy-4-methoxymethyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acidYield 71.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (1,6-dihydroxy-4-methoxymethyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid ethyl ester (0.20 g, 0.67 mmol) in THF (6 mL) and H2O (2 mL) was added LiOH (0.130 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 was purified by preparative HPLC to give (1,6-dihydroxy-4-methoxymethyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid (0.120 g, 71%). 1H NMR (400 MHz, DMSO-d6) δ 12.24 (s, 1H), 9.42 (s, 1H), 9.10 (s, 1H), 6.99 (s, 1H), 6.82 (s, 1H), 5.46 (m, 1H), 3.28 (s, 3H), 3.03 (m, 1H), 2.02 (m, 1H). MS (ESI) m/z: 251 [M−1]−. HPLC purity: 97.87% (220 nm), 98.47% (Maxplot).

Workup

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

Sources & evidence

ORD record
ord-09ea7cf6016a4440b7e3963c63d2bf99
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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