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

HRID 1798181Notes

Reaction equation

HRID 1798181 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.[OH-:27].[Na+].C[OH:30].C1COCC1>>[C:19]([CH2:18][CH:17]1[O:16][B:15]([OH:24])[C:14]2[CH:25]=[C:10]([O:9][C:5]3[CH:4]=[C:3]([CH:8]=[CH:7][N:6]=3)[C:1]([OH:30])=[O:27])[CH:11]=[C:12]([CH3:26])[C:13]1=2)([OH:21])=[O:20]

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 21899815MeOH tetrahydrofuranHCID 67253702Ethyl 2-(6-(4-cyanopyridin-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate

Product 1

HCID 509230912-(3-(Carboxymethyl)-1-hydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-6-yloxy)isonicotinic acid

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 9.20 (b 1H), 8.26 (d, J=5.2 Hz 1H), 7.47 (dd, J=5.2, 1.2 Hz, 1H), 7.29 (s, 1H), 7.17 (s, 1H), 7.02 (s, 1H), 5.46 (dd, J=9.6, 2.4 Hz, 1H), 3.03 (dd, J=16, 2.8 Hz, 1H), 2.24 (s, 3H), 2.08 (dd, J=15.2, 9.6 Hz, 1H). 2 protons assumed to be exchanged with solvents. MS (ESI) m/z=344 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-20655ce126f8422fa51854e8c57c1d73
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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