Sodium Hydroxide → HCID 10476846, compound

HRID 1582099Notes

Reaction equation

C([O:3][C:4](=[O:32])/[CH:5]=[C:6](\[CH3:31])/[CH:7]=[CH:8]/[C:9](/[F:30])=[C:10](\[C:12]1[CH:13]=[C:14]([CH:27]([CH3:29])[CH3:28])[CH:15]=[C:16]2[C:21]=1[N:20]([CH2:22][CH2:23][CH3:24])[CH2:19][CH2:18][C:17]2([CH3:26])[CH3:25])/[CH3:11])C.[OH-].[Na+]>>[F:30]/[C:9](=[C:10](/[C:12]1[CH:13]=[C:14]([CH:27]([CH3:28])[CH3:29])[CH:15]=[C:16]2[C:21]=1[N:20]([CH2:22][CH2:23][CH3:24])[CH2:19][CH2:18][C:17]2([CH3:26])[CH3:25])\[CH3:11])/[CH:8]=[CH:7]/[C:6](/[CH3:31])=[CH:5]/[C:4]([OH:32])=[O:3]

Participants

Reactant 2

HCID 14798Sodium Hydroxide

HCID 86759444HCID 86759444, compound2×

Product 1

HCID 10476846HCID 10476846, compound

Procedure

Following General Procedure I, (2E,4E,6E)-7-(1-n-propyl-6-isopropyl-4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-8-yl)-6-fluoro-3-methyl-octa-2,4,6-trienoic acid ethyl ester (Compound 26, 830 mg, 1.88 mmol) was hydrolyzed with NaOH to yield the title compound as a yellow solid after purification by column chromatography (silica, first using 100% hexane, followed by 5:95 ethyl acetate:hexane, then 1:1 ethyl acetate:hexane) to yield a yellow oil. The resulting yellow oil was recrystallized from acetonitrile.

Sources & evidence

ORD record: ord-9cda782f99a44484adedeaf9e8a57deb
Source dataset: uspto-grants-2004_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06734193B1

Reaction notes

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