Sodium Hydroxide → 2-[4-(4-Carboxymethylphenyl)-3-cyclohexen-1-yl]propyl 2-propanesulfonamide

HRID 279359Notes

Reaction equation

[C:1]([CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH2:15][CH2:14][CH:13]([CH:16]([CH3:25])[CH2:17][CH2:18][CH:19]([S:21]([NH2:24])(=[O:23])=[O:22])[CH3:20])[CH2:12][CH:11]=2)=[CH:6][CH:5]=1)#N.[OH-:26].[Na+].S(=O)(=O)(O)[O-:29].[Na+]>O1CCOCC1>[C:1]([CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH2:15][CH2:14][CH:13]([CH:16]([CH3:25])[CH2:17][CH2:18][CH:19]([S:21]([NH2:24])(=[O:23])=[O:22])[CH3:20])[CH2:12][CH:11]=2)=[CH:6][CH:5]=1)([OH:29])=[O:26]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of N-[2-[4-(4-cyanomethylphenyl)-3-cyclohexen-1-yl]propyl 2-propanesulfonamide (see Example 15) in dioxane is added 5 N sodium hydroxide. The mixture is heated to 100° C. for 24 hr. The mixture is then cooled, and acidified with 10% aqueous sodium bisulfate. The mixture is extracted three times with ethyl acetate and the combined organic extracts are dried, filtered and concentrated in vacuo to afford the title compound.

Workup

temperatureThe mixture is then cooled
extractionThe mixture is extracted three times with ethyl acetate
customthe combined organic extracts are dried
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-c492a67587874836829d7f95f2992b0d
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06362230B1

Reaction notes

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