Sodium Hydroxide → Pactimibe

HRID 1531962Notes

Reaction equation

[CH2:1]([N:9]1[C:17]2[C:12](=[C:13]([CH3:32])[C:14]([CH2:26][C:27]([O:29]CC)=[O:28])=[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].[OH-].[Na+]>CCO.O>[CH2:1]([N:9]1[C:17]2[C:12](=[C:13]([CH3:32])[C:14]([CH2:26][C:27]([OH:29])=[O:28])=[C:15]([CH3:25])[C:16]=2[NH:18][C:19](=[O:24])[C:20]([CH3:21])([CH3:22])[CH3:23])[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-ethoxycarbonylmethyl-4,6-dimethylindolin-7-yl)-2,2-dimethylpropanamide (3.0 g) was dissolved in EtOH (42 ml) and a solution of NaOH (1.4 g) in water (17 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 adjusted to pH 1-2 with nitric 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 2.0 g of the title compound. IR (Nujol)cm−1: 1724, 1654

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-418dc38314074fbf835abdbd2c297aa7
Source dataset: uspto-grants-2001_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06200988B1

Reaction notes

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