Hydrochloric Acid → HCID 67253902, compound

HRID 1798277Notes

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

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of [6-(6-cyano-pyridazin-3-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester (0.25 g, 0.7 mmol) in THF:H2O (1:1, 6 mL) at 0° C. was added a solution of LiOH (0.025 g, 1.06 ml) in water (1 mL). The solution was stirred at 0° C. for 20 hours then acidified to pH 3 with 1N HCl and extracted with EtOAc (2×10 mL). The organic extracts were dried and concentrated in vacuo. The residue was purified by preparative HPLC to give [6-(6-carbamoyl-pyridazin-3-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid (0.025 g, 11%) and [6-(6-cyano-pyridazin-3-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid (0.058 g, 26%).

Workup

extractionextracted with EtOAc (2×10 mL)
customThe organic extracts were dried
concentrationconcentrated in vacuo
customThe residue was purified by preparative HPLC

Sources & evidence

ORD record: ord-715c68ebf7fd432cadbec90cb70a87ce
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08343944B2

Reaction notes

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