Hydrochloric Acid → HCID 58292809, compound

HRID 1798222Notes

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:17][C:18]3[CH:23]=[N:22][CH:21]=[C:20]([C:24]#[N:25])[N:19]=3)[CH:14]=[C:15]([CH3:16])[C:7]1=2)C.[Li+].[OH-:28].Cl>C1COCC1.O>[C: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:26])=[O:3])[O:10][B:9]([OH:11])[C:8]=3[CH:12]=2)[CH:23]=[N:22][CH:21]=1)#[N:25].[C: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:3])=[O:26])[O:10][B:9]([OH:11])[C:8]=3[CH:12]=2)[CH:23]=[N:22][CH:21]=1)(=[O:28])[NH2:25]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution [6-(6-cyano-pyrazin-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid ethyl ester (0.2 g, 0.556 mmol) in THF (3 mL) was added a solution of LiOH (0.041 g, 1.69 mmol) in water (3 mL) at 0° C. The resulting mixture was stirred at 0° C. for 5 hours, 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-cyano-pyrazin-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid as a white solid (0.067 g) and [6-(6-carbamoyl-pyrazin-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid as a white solid (0.025 g).

Workup

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

Sources & evidence

ORD record: ord-20c7a80fceaf4cb79aebc69394e93e9f
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08343944B2

Reaction notes

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