Sodium Hydroxide → HCID 58292691, compound

HRID 1798188Notes

Reaction equation

HRID 1798188 reaction equation
[NH2:1][CH2:2][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.[OH-].[Na+]>CO.C1COCC1>[NH2:1][CH2:2][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

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58292837HCID 58292837, compound

Product 1

HCID 58292691HCID 58292691, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of crude ethyl 2-(6-(4-(aminomethyl)pyridin-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate 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, acidified to pH 3 with 1N 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), 8.33 (b, 2H), 8.18 (d, J=5.2 Hz, 1H), 7.17 (m, 2H), 7.11 (s, 1H), 7.00 (d, J=1.6 Hz, 1H), 5.50 (dd, J=10, 2.8 Hz, 1H), 4.10 (d, J=5.2 Hz, 2H), 3.07 (dd, J=15.2, 2.4 Hz, 1H), 2.29 (s, 3H), 2.12 (dd, J=15.6, 9.6 Hz, 1H). MS (ESI) m/z=329 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-fc5a0e31dfb34e99b3fec2109bbb5d06
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

Loading…