Hydrochloric Acid → HCID 67440422, compound

HRID 1483658Notes

Reaction equation

HRID 1483658 reaction equation
C([O:3][C:4](=[O:26])[CH2:5][O:6][C:7]1[CH:12]=[C:11]([O:13][C:14]2[CH:23]=[CH:22][C:17]3[B:18]([OH:21])[O:19][CH2:20][C:16]=3[CH:15]=2)[CH:10]=[CH:9][C:8]=1[C:24]#[N:25])C.[Li+].[OH-].O.Cl>C1COCC1>[C:24]([C:8]1[CH:9]=[CH:10][C:11]([O:13][C:14]2[CH:23]=[CH:22][C:17]3[B:18]([OH:21])[O:19][CH2:20][C:16]=3[CH:15]=2)=[CH:12][C:7]=1[O:6][CH2:5][C:4]([OH:26])=[O:3])#[N:25]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 67440776HCID 67440776, compound

Product 1

HCID 67440422HCID 67440422, compoundYield 59.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a clear solution of [2-cyano-5-(1-hydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-5-yloxy)-phenoxy]-acetic acid ethyl ester ((D38), 90 mg, 0.25 mmol) in THF (20 mL) was added LiOH (15.3 mg, 0.76 mmol) and water (5 mL). The resulting mixture was stirred at room temperature for 2 hours. Then 1 N HCl was slowly added to pH 2. The mixture was evaporated under vacuum. The residue was purified with reverse phase chromatography, eluting from 5% MeOH/H2O to 90% MeOH/H2O, afforded 48 mg of the title compound in 58% yield. 1H NMR 400 MHz (CD3OD) δ: 7.70 (d, J=7.8 Hz, 1H), 7.59 (d, J=8.6 Hz, 1H), 7.09 (s, 1H), 7.05 (dd, J=1.9, 8.21 Hz, 1H), 6.66 (d, J=1.9 Hz, 1H), 6.63 (dd, J=1.9, 8.6 Hz, 1H), 5.06 (s, 2H), 4.78 (s, 2H); MS (ES) m/z: 326 (M+H)1; HPLC purity: 96.33% (220 nm), 96.44% (254 nm).

Workup

  1. customThe mixture was evaporated under vacuum
  2. customThe residue was purified with reverse phase chromatography
  3. washeluting from 5% MeOH/H2O to 90% MeOH/H2O

Sources & evidence

ORD record
ord-1c5074a1526c4b668f0d2b1f1ccf16e7
Source dataset
uspto-grants-2016_08
Patent number
US09416146B2

Reaction notes

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