Sodium Hydroxide → HCID 67252719, compound

HRID 1798177Notes

Reaction equation

HRID 1798177 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:9][C:10]2[CH:11]=[C:12]([CH3:26])[C:13]3[CH:17]([CH2:18][C:19]([O:21]CC)=[O:20])[O:16][B:15]([OH:24])[C:14]=3[CH:25]=2)=[N:7][CH:8]=1)#[N:2].[OH-].[Na+]>CO.C1COCC1>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:9][C:10]2[CH:11]=[C:12]([CH3:26])[C:13]3[CH:17]([CH2:18][C:19]([OH:21])=[O:20])[O:16][B:15]([OH:24])[C:14]=3[CH:25]=2)=[N:7][CH:8]=1)#[N:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67252274HCID 67252274, compound

Product 1

HCID 67252719HCID 67252719, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-(6-(5-cyanopyridin-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate in MeOH/THF (12 mL, 1:1) was added aqueous NaOH solution (250 mg in 3 mL water). After stirring at room temperature for two hours, the reaction mixture was evaporated, acidified to pH 3 with 1 N HCl and then concentrated. HPLC purification gave product as a white powder. 1H NMR (400 MHz, DMSO-d6) δ 8.58 (s, 1H), 8.25 (dd, J=8.8, 2.4 Hz, 1H), 7.19 (m, 2H), 7.04 (s, 1H), 5.47 (dd, J=9.6, 2.4 Hz, 1H), 3.03 (dd, J=15.6, 2.4 Hz, 1H), 2.24 (s, 3H), 2.12 (dd, J=15.6, 9.6 Hz, 1H). 2 protons assumed to be exchanged with solvents. MS (ESI) m/z=323 [M−H]+.

Workup

  1. customthe reaction mixture was evaporated
  2. concentrationconcentrated
  3. customHPLC purification
  4. customgave product as a white powder

Sources & evidence

ORD record
ord-91480cd5586646a29f84e4f4b37ca515
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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