Sodium Hydroxide → HCID 58292788, compound

HRID 1798171Notes

Reaction equation

HRID 1798171 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([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:3]=1.[OH-].[Na+]>CO.C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([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:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58292764HCID 58292764, compound

Product 1

HCID 58292788HCID 58292788, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-(6-(4-chloropyridin-2-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 (200 mg in 2 mL of water). After stirring at room temperature for two hours, the reaction mixture was evaporated and 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 9.20 (b, 1H), 8.11 (d, J=5.2 Hz, 1H), 7.24 (dd, J=5.6, 2 Hz, 1H), 7.21 (d, m, 2H), 7.05 (d, J=1.6 Hz, 1H), 5.50 (dd, J=9.6, 2.4 Hz, 1H), 3.07 (dd, J=15.6, 2.8 Hz, 1H), 2.28 (s, 3H), 2.12 (dd, J=15.6, 9.6 Hz, 1H). 1 protons assumed to be exchanged with solvents. MS (ESI) m/z=334 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-a451ddb37c6943e99e3403acea6c8033
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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