Sodium Hydroxide → HCID 58292762, compound

HRID 1798163Notes

Reaction equation

HRID 1798163 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:10]=[C:11]([CH3:25])[C:12]3[CH:16]([CH2:17][C:18]([O:20]CC)=[O:19])[O:15][B:14]([OH:23])[C:13]=3[CH:24]=2)[CH:5]=[CH:4][N:3]=1.[OH-].[Na+]>CO.C1COCC1>[NH2:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:10]=[C:11]([CH3:25])[C:12]3[CH:16]([CH2:17][C:18]([OH:20])=[O:19])[O:15][B:14]([OH:23])[C:13]=3[CH:24]=2)[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58292740HCID 58292740, compound

Product 1

HCID 58292762HCID 58292762, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-(6-(2-aminopyridin-4-yloxy)-1-hydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate in MeOH/THF (8 mL, 1:1) was added aqueous NaOH solution (200 mg in 2 mL of water). After stirring at room temperature for two hours, the reaction mixture was evaporated, acidified to pH 5 using 1 M HCl and then concentrated. HPLC purification gave desired product as a white powder. 1H NMR (400 MHz, DMSO-d6) δ 12.3 (b, 1H), 9.30 (b, 1H), 7.87 (d, J=7.2 Hz, 1H), 7.69 (b, 2H), 7.25 (d, J=2 Hz, 1H), 7.13 (d, J=2 Hz, 1H), 6.59 (dd, J=7.2, 2.8 Hz, 1H), 6.00 (d, J=2.4 Hz, 1H), 5.49 (dd, J=9.6, 2.4 Hz, 1H), 3.05 (dd, J=15.6, 2.4 Hz, 1H), 2.28 (s, 3H), 2.08 (dd, J=15.2, 9.6 Hz, 1H). MS (ESI) m/z=313 [M−H]+.

Workup

  1. customthe reaction mixture was evaporated
  2. concentrationconcentrated
  3. customHPLC purification

Sources & evidence

ORD record
ord-c4272bb56f3e4a0e841ee680eabb9ae9
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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