Hydrochloric Acid → HCID 58292739, compound

HRID 1798193Notes

Reaction equation

HRID 1798193 reaction equation
C([O:3][C:4](=[O:25])[CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([O:18][C:19]3[N:24]=[CH:23][CH:22]=[CH:21][N:20]=3)[CH:14]=[C:15]([CH2:16][CH3:17])[C:7]1=2)C.[Li+].[OH-].Cl>C1COCC1.O>[CH2:16]([C:15]1[C:7]2[CH:6]([CH2:5][C:4]([OH:25])=[O:3])[O:10][B:9]([OH:11])[C:8]=2[CH:12]=[C:13]([O:18][C:19]2[N:20]=[CH:21][CH:22]=[CH:23][N:24]=2)[CH:14]=1)[CH3:17]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58292609HCID 58292609, compound

Product 1

HCID 58292739HCID 58292739, compoundYield 25.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [4-ethyl-1-hydroxy-6-(pyrimidin-2-yloxy)-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester (0.13 g, 0.38 mmol) in THF (8 mL) and H2O (2 mL) was added LiOH (0.091 g) at 0° C. The resulting mixture was stirred at room temperature for 2 hours then cooled to 0° C. and acidified to pH 3 with 6N HCl. The mixture was concentrated in vacuo and the residue purified by preparative HPLC to give [4-ethyl-1-hydroxy-6-(pyrimidin-2-yloxy)-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid (0.030 g, 25%). 1H NMR (400 MHz, DMSO-d6δ9.00 (br s, 1H), 8.63 (s, 1H), 8.62 (s, 1H), 7.25 (s, 1H), 7.24 (s, 1H), 7.23 (s, 1H), 7.10 (s, 1H), 5.51 (m, 1H), 3.01 (m, 1H), 2.61 (m, 2H), 2.14 (m, 1H), 1.17 (m, 3H). MS (ES) m/z: 313 (M−1)−. HPLC purity: 99.12% (220 nm), 98.58% (Maxplot).

Workup

  1. temperaturethen cooled to 0° C.
  2. concentrationThe mixture was concentrated in vacuo
  3. customthe residue purified by preparative HPLC

Sources & evidence

ORD record
ord-88420e897364406c829e90438da4223a
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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