Ethanol → Pactimibe

HRID 889789Notes

Reaction equation

[CH2:1]([N:9]1[C:17]2[C:12](=[C:13]([CH3:29])[C:14](OCC)=[C:15]([CH3:25])[C:16]=2[NH:18][C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:11][CH:10]1CC(O)=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[OH-:34].[Na+].[CH3:36][CH2:37][OH:38]>O>[CH2:1]([N:9]1[C:17]2[C:12](=[C:13]([CH3:29])[C:14]([CH2:36][C:37]([OH:34])=[O:38])=[C:15]([CH3:25])[C:16]=2[NH:18][C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:11][CH2:10]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

Conditions

Temperature: 60 °C

Procedure

N-(1-octyl-5-ethoxycarboxymethyl-4,6-dimethylindolin-7-yl)-2,2-dimethylpropanamide (3.5 g) was dissolved in EtOH (50 ml) and a solution of NaOH (1.6 g) in water (20 ml) was added, which was followed by stirring at 60° C. for 1 hr. EtOH was evaporated under reduced pressure. The residue was dissolved in water (20 ml) and the mixture was washed with AcOEt (20 ml). The aqueous layer was neutralized with 2N-hydrochloric acid and extracted with AcOEt (50 ml). The AcOEt layer was washed with saturated brine and dried over anhydrous sodium sulfate. AcOEt was evaporated under reduced pressure to give 2.4 g of the title compound.

Workup

customEtOH was evaporated under reduced pressure
dissolutionThe residue was dissolved in water (20 ml)
washthe mixture was washed with AcOEt (20 ml)
extractionextracted with AcOEt (50 ml)
washThe AcOEt layer was washed with saturated brine
dry with materialdried over anhydrous sodium sulfate
customAcOEt was evaporated under reduced pressure

Sources & evidence

ORD record: ord-1298b7f2e77c472697c01440f23c54c0
Source dataset: uspto-grants-2006_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: USRE038970E1

Reaction notes

Loading…