Sodium Hydroxide → HCID 60086016, compound

HRID 1582098Notes

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

Participants

Reactant 2

HCID 14798Sodium Hydroxide

HCID 86759446HCID 86759446, compound2×

Product 1

HCID 60086016HCID 60086016, compound

Procedure

Following General Procedure I, (2E,4E,6E)-7-(1-ethyl-6-isopropyl-4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-8-yl)-6-fluoro-3-methyl-nona-2,4,6-trienoic acid ethyl ester (Compound 25, 630 mg, 14.3 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-9be7a36f68ec495b9daa57153c4df93c
Source dataset: uspto-grants-2004_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06734193B1

Reaction notes

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