Sodium Hydroxide → HCID 58292806, compound

HRID 1798160Notes

Reaction equation

HRID 1798160 reaction equation
[Cl: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>[Cl: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 58292747HCID 58292747, compound

Product 1

HCID 58292806HCID 58292806, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-(6-(2-chloropyridin-4-yloxy)-1-hydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate in MeOH/THF (6 mL, 1:1) was added aqueous NaOH solution (100 mg in 1.5 mL of water). After stirring at room temperature for two hours, the reaction mixture was evaporated and then acidified to pH 3 using 1 M HCl. This was then extracted with EtOAc, the organic layers were combined, washed by brine and concentrated. HPLC purification gave desired product as a white powder. 1H NMR (400 MHz, DMSO-d6) δ 9.2 (b, 1H), 8.23 (d, J=6 Hz, 1H), 7.22 (s, 1H), 7.09 (s, 1H), 6.95 (s, 1H), 6.88 (dd, J=6, 2 Hz, 1H), 5.49 (dd, J=9.2, 2.4 Hz, 1H), 3.04 (dd, J=15.6, 2.8 Hz, 1H), 2.28 (s, 3H), 2.13 (dd, J=15.2, 9.2 Hz, 1H). 1 proton assumed to be exchanged with solvents. MS (ESI) m/z=332 [M−H]+.

Workup

  1. customthe reaction mixture was evaporated
  2. extractionThis was then extracted with EtOAc
  3. washwashed by brine
  4. concentrationconcentrated
  5. customHPLC purification

Sources & evidence

ORD record
ord-64efed3985a24ed98dd9b6739a887f27
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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