Hydrochloric Acid → HCID 58292833, compound

HRID 1798215Notes

Reaction equation

HRID 1798215 reaction equation
C([O:3][C:4](=[O:25])[CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([O:17][C:18]3[CH:23]=[N:22][CH:21]=[C:20]([Cl:24])[N:19]=3)[CH:14]=[C:15]([CH3:16])[C:7]1=2)C.[Li+].[OH-].Cl>C1COCC1.O>[Cl:24][C:20]1[N:19]=[C:18]([O:17][C:13]2[CH:14]=[C:15]([CH3:16])[C:7]3[CH:6]([CH2:5][C:4]([OH:25])=[O:3])[O:10][B:9]([OH:11])[C:8]=3[CH:12]=2)[CH:23]=[N:22][CH:21]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58292588HCID 58292588, compound

Product 1

HCID 58292833HCID 58292833, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [6-(6-chloro-pyrazin-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid ethyl ester (0.11 g, 0.30 mmol) in THF (3 mL) was added a solution of LiOH (0.036 g, 1.5 mmol) in water (1 mL) at 0° C. The resulting mixture was stirred at room temperature for 2 hours then acidified to pH 2 using 6M hydrochloric acid and extracted with EtOAc. The organic extracts were washed with water, brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by preparative HPLC to give [6-(6-chloro-pyrazin-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid as an off white solid (0.05 g, 50%). mp 187.2-188° C. 1H NMR (400 MHz, DMSO-d δ 12.34 (s, 1H), 9.26 (s, 1H), 8.54 (s, 1H), 8.51 (s, 1H), 7.31 (s, 1H), 7.17 (s, 1H), 5.55 (m, 1H), 3.10 (dd, J=15.60, 2.80 Hz, 1H), 2.32 (s, 3H), 2.16 (m, 1H). MS (ESI) m/z: 333 (M−1)−. HPLC purity: 98.97% (Maxplot), 99.14% (220 nm).

Workup

  1. extractionextracted with EtOAc
  2. washThe organic extracts were washed with water, brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-3d4f4293f44f46d982163b06f3243c2e
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

Loading…