(Diethylamino)sulfur trifluoride → HCID 25029412, compound

HRID 1436404Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([N:13]3[C@H:17]([CH2:18]O)[CH2:16][O:15][C:14]3=[O:20])[S:11][CH:12]=2)=[CH:4][CH:3]=1.C(N(S(F)(F)[F:27])CC)C>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([N:13]3[C@H:17]([CH2:18][F:27])[CH2:16][O:15][C:14]3=[O:20])[S:11][CH:12]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 25 °C

Procedure

(4R)-3-[4-(4-Bromophenyl)-1,3-thiazol-2-yl]-4-(hydroxymethyl)-1,3-oxazolidin-2-one (0.71 g, 2.0 mmol), prepared in Example 71, was dissolved in 20 mL methylene chloride and cooled to 0° C. (Diethylamino)sulfur trifluoride (0.295 mL, 2.20 mmol) was added dropwise. The mixture was warmed to 25° C. and stirred for 2.5 h. The reaction was quenched with water and saturated NaHCO3 and the mixture was extracted with methylene chloride. The organics were combined and washed with water, brine, dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. Flash chromatography (8% acetone/hexane) afforded the title compound (243 mg, 34%) as a white solid. mp 148-150° C. HRMS: calcd for C13H10BrFN2O2S+H+, 356.97031; found (ESI, [M+H]+), 356.9705. Analytical HPLC: retention time 10.2 min, 210-370 nm the Xterra® RP18 column, 3.5μ, 150×4.6 mm 40° C. 85/15-5/95 (Ammon. Form. Buff. pH 3.5/ACN+MeOH) for 10 min, hold 4 min, 1.2 mL/min 5 μL injection.

Workup

additionwas added dropwise
customThe reaction was quenched with water and saturated NaHCO3
extractionthe mixture was extracted with methylene chloride
washwashed with water, brine
dry with materialdried over anhydrous MgSO4
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-4ac6340d3e7d4be5b9a375ae2ce8729d
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07618990B2

Reaction notes

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