Hydrochloric Acid → HCID 58292859, compound

HRID 1798146Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

An ice-cold yellow solution of (1-hydroxy-4-methyl-6-phenoxy-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid ethyl ester G45 (0.19 g, 0.58 mmol) in MeOH (3 mL) was treated with lithium hydroxide (0.07 g, 2.92 mmol, in 2 mL of H2O) dropwise. The mixture was stirred at 0° C. for 2 h, then rt for 3 h. The mixture was acidified with 2 N HCl to pH 3, then extracted with EtOAc, dried (Na2SO4), filtered and concentrated to a yellow oil. The oil was purified by column chromatography (SiO2, AcOH/EtOAc/hexanes; 0.5:4:100) to afford 1-hydroxy-4-methyl-6-phenoxy-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid (0.14 g, 83%), as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ 12.27 (br s, 1H), 9.16 (s, 1H), 7.40 (t, J=7.42 Hz, 2H), 7.14 (t, J=7.42 Hz, 1H), 7.07 (d, J=2.35 Hz, 1H), 7.06-6.97 (m, 3H), 5.48 (dd, J=9.38, 2.34 Hz, 1H), 3.05 (dd, J=15.44, 2.74 Hz, 1H), 2.29 (s, 3H), 2.16-2.06 (m, 1H); MS (ES) m/z: 297 (M−1).

Workup

waitrt for 3 h
extractionextracted with EtOAc
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated to a yellow oil
customThe oil was purified by column chromatography (SiO2, AcOH/EtOAc/hexanes; 0.5:4:100)
customto afford 1-hydroxy-4-methyl-6-phenoxy-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid (0.14 g, 83%)

Sources & evidence

ORD record: ord-1aec8290e73c458fb4a4186124e7d7e2
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08343944B2

Reaction notes

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