Hydrochloric Acid → HCID 86653983, compound

HRID 1798209Notes

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

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution [6-(6-cyano-pyrimidin-4-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-pyrimidin-4-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid as a white solid (0.015 g). 1H NMR (400 MHz, DMSO-d δ 9.18 (s, 1H), 8.82 (d, J=10.0 Hz, 1H), 7.45 (d, J=6.0 Hz, 1H), 7.30 (s, 1H), 7.16 (s, 1H), 5.51 (m, 1H), 3.07 (m, 1H), 2.31 (s, 3H), 2.16 (m, 1H). MS (ESI) m/z: 324 [M−1]−. HPLC purity: 96.94% (Maxplot), 98.24% (220 nm).

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-6e334f940d8a4b1e8322feeb4b08f85c
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08343944B2

Reaction notes

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