Sodium Hydroxide → HCID 22247343, compound

HRID 1531991Notes

Reaction equation

[CH2:1]([N:9]1[C:18]2[C:13](=[C:14]([CH3:33])[C:15]([CH2:27][C:28]([O:30]CC)=[O:29])=[C:16]([CH3:26])[C:17]=2[NH:19][C:20](=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:12][CH2:11][CH2:10]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[OH-].[Na+]>C(O)C.O>[CH2:1]([N:9]1[C:18]2[C:13](=[C:14]([CH3:33])[C:15]([CH2:27][C:28]([OH:30])=[O:29])=[C:16]([CH3:26])[C:17]=2[NH:19][C:20](=[O:25])[C:21]([CH3:22])([CH3:23])[CH3:24])[CH2:12][CH2:11][CH2:10]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

Conditions

Temperature: 50 °C

Procedure

N-(1Octyl-6-ethoxycarbonylmethyl-5,7-dimethyl-1,2,3,4-tetrahydro-quinolin-8-yl)-2,2-dimethylpropanamide (230 mg) was dissolved in ethanol (5 ml), and a solution of NaOH (100 mg) in water (2 ml) was added, which was followed by stirring at 50° C. for 1 hr. The solvent of the reaction mixture was evaporated under reduced pressure. The residue was dissolved in water (50 ml) and washed with ethyl acetate (20 ml). The aqueous layer was adjusted to pH 1-2 with 2N sulfuric acid and extracted with chloroform. The chloroform layer was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give 130 mg of powdery title compound. TLC; Silica gel 60F254 Art. 5714 (Merck), CHCl3-MeOH (10:1), Rf value 0.5.

Workup

customThe solvent of the reaction mixture was evaporated under reduced pressure
dissolutionThe residue was dissolved in water (50 ml)
washwashed with ethyl acetate (20 ml)
extractionextracted with chloroform
dry with materialThe chloroform layer was dried over anhydrous sodium sulfate
customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-c1bf5768ee0944b687a8919e6d51f474
Source dataset: uspto-grants-2001_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06200988B1

Reaction notes

Loading…