Hydrochloric Acid → N-(5-fluoro-2-oxo-2,3-dihydro-1H-indol-6-yl)-2-hydroxy-2-methyl-propionamide

HRID 2191419Notes

Reaction equation

HRID 2191419 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[NH:11][C:12]([C:14]([O:17]C(=O)C)([CH3:16])[CH3:15])=[O:13])[NH:7][C:6](=[O:21])[CH2:5]2.[OH-].[Na+].Cl>CO>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[NH:11][C:12](=[O:13])[C:14]([OH:17])([CH3:16])[CH3:15])[NH:7][C:6](=[O:21])[CH2:5]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59250100acetic acid 1-(5-fluoro-2-oxo-2,3-dihydro-1H-indol-6-ylcarbamoyl)-1-methyl-ethyl ester

Product 1

HCID 59250047N-(5-fluoro-2-oxo-2,3-dihydro-1H-indol-6-yl)-2-hydroxy-2-methyl-propionamideYield 59.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Acetic acid 1-(5-fluoro-2-oxo-2,3-dihydro-1H-indol-6-ylcarbamoyl)-ethyl ester 9a (2.035 g, 6.9 mmol) was dissolved in 20 ml of methanol under stirring, added with sodium hydroxide solution (20 ml, 0.7 mol/L) (20 ml) to the solution and stirred for 4 hours at room temperature. After thin lay chromatography showed the disappearance of starting materials, the reaction mixture was neutralized with hydrochloride acid (1 mol/L) and concentrated under reduced pressure. The residue was purified by silica gel column chromatography and dried to obtain N-(5-fluoro-2-oxo-2,3-dihydro-1H-indol-6-yl)-2-hydroxy-2-methyl-propionamide 9b (900 mg, yield 59.2%) as a white solid.

Workup

  1. stirringstirred for 4 hours at room temperature
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography
  4. customdried

Sources & evidence

ORD record
ord-12db0ffda36644fea025ee66cd7b61da
Source dataset
uspto-grants-2012_12
Patent number
US08329682B2

Reaction notes

Loading…