Lawesson's reagent → (S)-5-Benzyl-4-((2-(trifluoromethoxy)phenyl)sulfonyl)-1,4-diazocane-2-thione

HRID 1429413Notes

Reaction equation

[CH2:1]([C@@H:8]1[CH2:15][CH2:14][CH2:13][NH:12][C:11](=O)[CH2:10][N:9]1[S:17]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[O:26][C:27]([F:30])([F:29])[F:28])(=[O:19])=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:40]2)=CC=1.C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1>[CH2:1]([C@@H:8]1[CH2:15][CH2:14][CH2:13][NH:12][C:11](=[S:40])[CH2:10][N:9]1[S:17]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[O:26][C:27]([F:30])([F:29])[F:28])(=[O:19])=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of compound 31m (500 mg, 1.13 mmol) in toluene (30 mL) was treated with 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide (Lawesson's reagent) (457 mg, 1.13 mmol), heated at 80° C. for 30 min, cooled to rt, treated with NaHCO3 (95 mg, 1.13 mmol) and stirred for 10 min. The mixture was extracted with EA three times and the combined organic layer was washed with brine and dried over anhydrous Na2SO4. After filtration, the filtrate was evaporated and the residue was purified by CC (hexane/EA=4:1) to give compound 31n (491 mg, 95% yield).

Workup

temperaturecooled to rt
extractionThe mixture was extracted with EA three times
washthe combined organic layer was washed with brine
dry with materialdried over anhydrous Na2SO4
filtrationAfter filtration
customthe filtrate was evaporated
customthe residue was purified by CC (hexane/EA=4:1)

Sources & evidence

ORD record: ord-0d39f88597fd449e850158dc44c2dd21
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08940722B2

Reaction notes

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