Dimethyl Sulfoxide → HCID 9841018, compound

HRID 1457327Notes

Reaction equation

[C:1]1([S:7]([C:10]2[CH:24]=[CH:23][CH:22]=[CH:21][C:11]=2[C:12]([N:14]2[CH2:18][CH2:17][CH2:16][CH:15]2[CH2:19][OH:20])=[O:13])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CS(C)=O.FC(F)(F)C(OC(=O)C(F)(F)F)=O.C(N(CC)CC)C>C(Cl)Cl>[C:1]1([S:7]([C:10]2[CH:24]=[CH:23][CH:22]=[CH:21][C:11]=2[C:12]([N:14]2[CH2:18][CH2:17][CH2:16][CH:15]2[CH:19]=[O:20])=[O:13])(=[O:8])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 0 °C

Procedure

0.6 g (1.7 mmol) of 1-[2-(phenylsulfonyl)benzoyl]-2-pyrrolidinemethanol in 0.73 ml (10 mmol) of dimethylsulfoxide (DMSO) and 20 ml methylene chloride was cooled to -70° C. 1.0 ml (6.8 mmol) of trifluoroacetic anhydride (TFAA) as added such that the temperature remained below -50° C. The reaction mixture was then stirred for 2 hours at between -50° and -70° C. 1.9 ml (14 mmol) of triethylamine was added and the mixture allowed to warm to 0° C. The reaction was quenched with water and the mixture was dried and evaporated to give an oil which was chromatographed on silica gel with chloroform to yield 0.2 g (34%) of the title compound. 1H NMR (CDCl3) δ: 9.70(m,1H); 8.10-8.20(m,3H); 7.20-7.70(m,6H); 4.70(m,1H); 3.30-3.50 (m,2H); 1.70-2.30(m,4H). High Resolution Mass Spectrum: m/e=344.0951±0.6 ppm (calculated for C18H18NO4S).

Workup

customremained below -50° C
customThe reaction was quenched with water
customthe mixture was dried
customevaporated
customto give an oil which
customwas chromatographed on silica gel with chloroform

Sources & evidence

ORD record: ord-abd2fe4505524aa39c5b584c83a59a58
Source dataset: uspto-grants-1998_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05847155

Reaction notes

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