Sodium Hydroxide → HCID 58292847, compound

HRID 1798173Notes

Reaction equation

HRID 1798173 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([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)=[N:7][CH:8]=1.[OH-].[Na+]>CO.C1COCC1>[NH2:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([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)=[N:7][CH:8]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58292718HCID 58292718, compound

Product 1

HCID 58292847HCID 58292847, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-(6-(5-(aminomethyl)pyridin-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 3 using 1 M HCl. The precipitate was collected and washed with water and dried to give the product as a white solid (0.85 g, yield 78%). No right mass was observed and the structure was confirmed by NMR. 1H NMR (400 MHz, DMSO-d6) δ 12.4 (b, 1H), 9.80 (b, 2H), 9.22 (s, 1H), 8.26 (d, J=2 Hz, 1H), 8.07 (m, 1H), 7.21 (d, J=2 Hz, 1H), 7.08 (d, J=8.4 Hz, 1H), 7.01 (m, 1H), 5.51 (dd, J=9.2, 4 Hz, 1H), 4.15 (s, 2H), 3.07 (dd, J=15.6, 2.4 Hz, 1H), 2.28 (s, 3H), 2.12 (dd, J=15.2, 9.6 Hz, 1H).

Workup

  1. customthe reaction mixture was evaporated
  2. customThe precipitate was collected
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-14e81f8fab3a4fcb89508310adf40e2b
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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