Tetrahydrofuran → HCID 86672533, compound

HRID 541307Notes

Reaction equation

[C:1]([C:3]1[C:4]([CH2:14][CH:15]2[CH2:18][CH2:17][CH2:16]2)=[CH:5][C:6]([CH3:13])=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9])#[N:2].C1COCC1.P(OCC)(OCC)([S-])=[S:25]>O>[C:1]([C:3]1[C:4]([CH2:14][CH:15]2[CH2:16][CH2:17][CH2:18]2)=[CH:5][C:6]([CH3:13])=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9])(=[S:25])[NH2:2]

Participants

Conditions

Temperature: 80 °C

Procedure

To a round-bottom flask was added a solution of methyl 5-cyano-4-(cyclobutylmethyl)-2-methylbenzoate (compound 189.3, 5.00 g, 20.6 mmol, 1.00 equiv) in a solvent mixture of THF and H2O (50 mL/25 mL). O,O′-diethyl dithiophosphate (15.0 g, 80.5 mmol, 4.00 equiv) was added to the reaction flask. The resulting solution was stirred at 80° C. for 48 h (CAUTION: significant gas evolution occurs—this and all other reactions described herein should be carried out in well ventilated fume hoods). After cooling to ambient temperature, the reaction was carefully quenched with 50 mL of brine. The mixture was extracted with 3×50 mL of ethyl acetate and the combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified using silica gel column chromatography with ethyl acetate/petroleum ether (1:4) as eluent to furnish 1.20 g (21%) of the title compound as a yellow oil.

Workup

temperatureAfter cooling to ambient temperature
customthe reaction was carefully quenched with 50 mL of brine
extractionThe mixture was extracted with 3×50 mL of ethyl acetate
dry with materialthe combined organic layers were dried over anhydrous sodium sulfate
concentrationconcentrated in vacuo
customThe residue was purified

Sources & evidence

ORD record: ord-619855a8b9ca45998df8a3bceac06827
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871790B2

Reaction notes

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