Sodium Hydroxide → HCID 58292763, compound

HRID 1798175Notes

Reaction equation

HRID 1798175 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-:27].[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)(=[O:27])[NH2:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67252274HCID 67252274, compound

Product 1

HCID 58292763HCID 58292763, 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 8.55 (d, J=2 Hz, 1H), 8.20 (dd, J=8.4, 2.4 Hz, 1H), 7.96 (s, 1H), 7.41 (s, 1H), 7.17 (d, J=1.6 Hz, 1H), 7.02 (d, J=8.4 Hz, 1H), 5.46 (dd, J=9.6, 2.4 Hz, 1H), 3.02 (dd, J=15.6, 2.4 Hz, 1H), 2.24 (s, 3H), 2.09 (dd, J=15.2, 9.6 Hz, 1H). 3 protons assumed to be exchanged with solvents. MS (ESI) m/z=341 [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-4b9626c6c5aa49ad84a25b19ffd7c3ac
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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