Hydrochloric Acid → HCID 58292721, compound

HRID 1798196Notes

Reaction equation

HRID 1798196 reaction equation
C([O:3][C:4](=[O:27])[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][N:21]=[C:20]([N:24]([CH3:26])[CH3:25])[N:19]=3)[CH:14]=[C:15]([CH3:16])[C:7]1=2)C.[OH-].[Li+].Cl>C1COCC1.O>[CH3:26][N:24]([CH3:25])[C:20]1[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:27])=[O:3])[O:10][B:9]([OH:11])[C:8]=3[CH:12]=2)[CH:23]=[CH:22][N:21]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58292687HCID 58292687, compound

Product 1

HCID 58292721HCID 58292721, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of [6-(2-dimethylamino-pyrimidin-4-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester (0.094 g, 0.25 mmol) in THF (5 mL) was treated with lithium hydroxide (0.029 g, 1.27 mmol) in water (0.5 mL) at 0° C. The solution was stirred at 0° C. to room temperature for 2 hours, then acidified with 2N HCl to pH 2, and concentrated. The residue was purified by silica gel flash column chromatography (AcOH:acetone:hexanes; trace:1:2; then MeOH:CH2Cl2; 5:95) to give [6-(2-dimethylamino-pyrimidin-4-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid as a white solid after lyophilization (0.02 g, 23%). 1H NMR (400 MHz, DMSO-d6) δ 8.18 (d, J=5.47 Hz, 1H), 7.24 (s, 1H), 7.07 (s, 1H), 6.01 (d, J=5.47 Hz, 1H), 5.50-5.45 (m, 1H), 3.02 (dd, J=15.63, 2.40 Hz, 1H), 2.96 (s, 6H), 2.28 (s, 3H), 2.11 (dd, J=15.63, 9.38 Hz, 1H). MS (ESI) m/z: 344 [M+1].

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by silica gel flash column chromatography (AcOH

Sources & evidence

ORD record
ord-2099deb47d894610b488a20b669e0720
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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