Hydrochloric Acid → HCID 57969228, compound

HRID 1471476Notes

Reaction equation

HRID 1471476 reaction equation
[C:1]([C:4]1[CH:20]=[CH:19][C:7]([O:8][C:9]2[CH:10]=[CH:11][C:12]3[B:16]([OH:17])[O:15][CH2:14][C:13]=3[CH:18]=2)=[CH:6][C:5]=1[C:21]([O:23]C)=O)(=[O:3])[NH2:2].[OH-].[Na+].Cl>CO>[OH:17][B:16]1[C:12]2[CH:11]=[CH:10][C:9]([O:8][C:7]3[CH:6]=[C:5]4[C:4](=[CH:20][CH:19]=3)[C:1](=[O:3])[NH:2][C:21]4=[O:23])=[CH:18][C:13]=2[CH2:14][O:15]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 57969005HCID 57969005, compound

Product 1

HCID 57969228HCID 57969228, compoundYield 75.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 5-(4-Carbamoyl-3-methoxycarbonylphenoxy)-1-hydroxy-2,1-benzoxaborole (560 mg, 1.71 mmol) and 1 M NaOH (5 mL) in methanol (15 mL) was stirred at room temperature for 10 min. The mixture was acidified with 6 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 triturated with ethyl acetate to give 5-(1,3-Dihydro-1-hydroxy-2,1-benzoxaborol-5-yloxy)isoindoline-1,3-dione (380 mg, 75%).

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. customthe residue was triturated with ethyl acetate

Sources & evidence

ORD record
ord-fac484d56a224242a7fcfa80e5a26f3b
Source dataset
uspto-grants-2015_04
Patent number
US09012431B2

Reaction notes

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