Hydrochloric Acid → HCID 58292604, compound

HRID 1798242Notes

Reaction equation

HRID 1798242 reaction equation
C([O:3][C:4](=[O:26])[CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([O:19][C:20]3[CH:25]=[N:24][CH:23]=[CH:22][N:21]=3)[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]([O:19][C:20]3[CH:25]=[N:24][CH:23]=[CH:22][N:21]=3)[CH:14]=[C:15]([CH2:16][O:17][CH3:18])[C:7]=2[CH:6]([CH2:5][C:4]([OH:26])=[O:3])[O:10]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58292821HCID 58292821, compound

Product 1

HCID 58292604HCID 58292604, compoundYield 81.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [1-hydroxy-4-methoxymethyl-6-(pyrazin-2-yloxy)-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester (0.20 g, 0.56 mmol) in THF (6 mL) and H2O (2 mL) was added LiOH (0.110 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 silica gel flash column chromatography to give [1-hydroxy-4-methoxymethyl-6-(pyrazin-2-yloxy)-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid (0.150 g, 81%). 1H NMR (400 MHz, DMSO-d6) δ 12.33 (s, 1H), 9.27 (s, 1H), 8.58 (s, 1H), 8.39 (s, 1H), 8.21 (s, 1H), 7.40 (s, 1H), 7.26 (s, 1H), 5.60 (s, 1H), 4.50 (m, 2H), 3.30 (s, 3H), 3.10 (m, 1H), 2.17 (m, 1H). MS (ESI) m/z: 329 [M−1]−. HPLC purity: 97.28% (220 nm), 96.84% (Maxplot).

Workup

  1. temperaturethen cooled to 0° C.
  2. concentrationThe mixture was concentrated in vacuo
  3. customthe residue purified by silica gel flash column chromatography

Sources & evidence

ORD record
ord-ea4364b8f8b241f89ebf7f7b27c5d3ec
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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