Methanol → 1-(4-Methoxybutyl)-3,3-dimethyl-2-oxoindoline-6-carboxylic acid

HRID 1942538Notes

Reaction equation

[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:16]([O:18]C)=[O:17])[CH:14]=2)[C:9]([CH3:21])([CH3:20])[C:8]1=[O:22].[OH-].[Na+].CO>C1COCC1>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:16]([OH:18])=[O:17])[CH:14]=2)[C:9]([CH3:20])([CH3:21])[C:8]1=[O:22]

Participants

Conditions

Temperature: 65 °C

Procedure

To methyl 1-(4-methoxybutyl)-3,3-dimethyl-2-oxoindoline-6-carboxylate (480 mg) were added 2N aqueous NaOH solution (5 ml), MeOH (5 ml), and THF (5 ml), and the mixture was stirred at 65° C. for one hour. After the reaction was complete, the solvent was concentrated, and to the resultant was added dropwise 2N aqueous hydrochloric acid solution. The precipitated crystals were extracted with ethyl acetate, and this ethyl acetate solution was washed with water and an aqueous sodium chloride solution, dried over magnesium sulfate, filtered, and concentrated. The obtained residue (400 mg) was used in the subsequent reaction without further treatment.

Workup

concentrationthe solvent was concentrated
additionto the resultant was added dropwise 2N aqueous hydrochloric acid solution
extractionThe precipitated crystals were extracted with ethyl acetate
washthis ethyl acetate solution was washed with water
dry with materialan aqueous sodium chloride solution, dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated
customThe obtained residue (400 mg) was used in the subsequent reaction without further treatment

Sources & evidence

ORD record: ord-910e1a4e7a7f408c97c4b501b9c5980e
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08389511B2

Reaction notes

Loading…