Hydrochloric Acid → HCID 67439337, compound

HRID 1483633Notes

Reaction equation

HRID 1483633 reaction equation
[C:1]([C:3]1[CH:19]=[CH:18][C:6]([O:7][C:8]2[CH:9]=[CH:10][C:11]3[B:15]([OH:16])[O:14][CH2:13][C:12]=3[CH:17]=2)=[C:5]([O:20][CH2:21][C:22]([O:24]CC)=[O:23])[CH:4]=1)#[N:2].[OH-].[Na+].Cl>CO>[C:22]([CH2:21][O:20][C:5]1[CH:4]=[C:3]([C:1]#[N:2])[CH:19]=[CH:18][C:6]=1[O:7][C:8]1[CH:9]=[CH:10][C:11]2[B:15]([OH:16])[O:14][CH2:13][C:12]=2[CH:17]=1)([OH:24])=[O:23]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67440007HCID 67440007, compound

Product 1

HCID 67439337HCID 67439337, compoundYield 41.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 5-[4-Cyano-2-(ethoxycarbonylmethoxy)phenoxy]-1,3-dihydro-1-hydroxy-2,1-benzoxaborole (D16) (216 mg, 0.612 mmol) and 1 M NaOH (2 mL in methanol (8 mL) was stirred at room temperature for 1 h. The mixture was acidified with 1 M HCl and extracted with ethyl acetate. The organic layer was washed with brine and dried on anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was treated with hexane to give 5-[2-(Carboxymethoxy)-4-cyanophenoxy]-1,3-dihydro-1-hydroxy-2,1-benzoxaborole (82 mg, 41%)

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried on anhydrous sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. additionthe residue was treated with hexane

Sources & evidence

ORD record
ord-57d78251f2eb4c749dcad818bee20a5a
Source dataset
uspto-grants-2016_08
Patent number
US09416146B2

Reaction notes

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