Ethyl Acetate → HCID 71230545, compound

HRID 401836Notes

Reaction equation

[CH3:1][C:2]([CH3:27])([CH3:26])[C:3]#[C:4][C:5]1[S:9][C:8]([C:10]([OH:12])=[O:11])=[C:7]([N:13]([CH:23]([CH3:25])[CH3:24])[C:14]([C@H:16]2[CH2:21][CH2:20][C:19]([CH3:22])=[CH:18][CH2:17]2)=[O:15])[CH:6]=1.[CH3:28]C(C)(C)C#CC1SC(C(OC)=O)=C(NC(C)C)C=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].CCOC(C)=O>ClC(Cl)C>[CH3:1][C:2]([CH3:26])([CH3:27])[C:3]#[C:4][C:5]1[S:9][C:8]([C:10]([O:12][CH3:28])=[O:11])=[C:7]([N:13]([CH:23]([CH3:24])[CH3:25])[C:14]([C@H:16]2[CH2:21][CH2:20][C:19]([CH3:22])=[CH:18][CH2:17]2)=[O:15])[CH:6]=1

Participants

Conditions

Temperature: 90 °C

Procedure

4-Methyl-cyclohex-3-enecarbonyl chloride (S) (0.71 mmol), methyl 5-(3,3-dimethylbut-1-ynyl)-3-(isopropylamino)thiophene-2-carboxylate (80 mg, 0.29 mmol) and potassium phosphate tribasic (152 mg, 0.71 mmol) were suspended in dichloroethane (0.75 mL), sealed with a cap and heated to 90° C. After 16 h, the reaction mixture was cooled and partitioned between ethyl acetate and water. The organic layer was separated and the aqueous extracted again with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and concentrated. Flash chromatography (10-35% EtOAc:Hexanes) afforded 59 mg (51% yield) of the desired (S)-methyl 5-(3,3-dimethylbut-1-ynyl)-3-(N-isopropyl-4-methylcyclohex-3-enecarboxamido)thiophene-2-carboxylate as a white foam.

Workup

customsealed with
customa cap
temperaturethe reaction mixture was cooled
custompartitioned between ethyl acetate and water
customThe organic layer was separated
extractionthe aqueous extracted again with ethyl acetate
dry with materialThe combined organic layers were dried over sodium sulfate
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-1f21ef1d9857471a9a42b1d14589b6c6
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08741946B2

Reaction notes

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