Sodium Hydroxide → 2-(6-(4-Carbamoylpyridin-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetic acid

HRID 1798183Notes

Reaction equation

HRID 1798183 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][N:6]=[C:5]([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)[CH:4]=1)#[N:2].[OH-:27].[Na+]>CO.C1COCC1>[C:1]([C:3]1[CH:8]=[CH:7][N:6]=[C:5]([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)[CH:4]=1)(=[O:27])[NH2:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67253702Ethyl 2-(6-(4-cyanopyridin-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate

Product 1

HCID 582927362-(6-(4-Carbamoylpyridin-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetic acid

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-(6-(4-cyanopyridin-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate (1.18 g, 3.31 mmol) 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 and then acidified to pH 5 using 1 N HCl and then concentrated. HPLC purification gave desired product as a white powder. 1H NMR (400 MHz, DMSO-d6) δ 12.4 (b, 1H), 9.20 (b, 1H), 8.20 (m, 2H), 7.70 (s, 1H), 7.44 (dd, J=5.6, 1.6 Hz, 1H), 7.33 (s, 1H), 7.15 (d, J=2 Hz, 1H), 7.00 (d, J=2 Hz, 1H), 5.46 (dd, J=9.6, 2.4 Hz, 1H), 3.03 (dd, J=15.6, 2.8 Hz, 1H), 2.44 (s, 3H), 2.08 (dd, J=15.6, 9.6 Hz, 1H). MS (ESI) m/z=343 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-e09fd92b70cd4fe88c9e0dffde472295
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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