(Diethylamino)sulfur trifluoride → HCID 178494571, compound

HRID 1900060Notes

Reaction equation

HRID 1900060 reaction equation
O[C@H:2]1[CH2:7][CH2:6][C@H:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:18][CH:17]([CH2:19][O:20][CH3:21])[O:16][C:15]3=[O:22])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.C(N(S(F)(F)[F:29])CC)C>C(Cl)Cl>[F:29][C@@H:2]1[CH2:7][CH2:6][C@H:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:18][CH:17]([CH2:19][O:20][CH3:21])[O:16][C:15]3=[O:22])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 178494572HCID 178494572, compound

Product 1

HCID 178494571HCID 178494571, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

0.5 g of (RS)3-[4-(trans-4-hydroxy-cyclohexyl)-phenyl]-5-methoxymethyl-oxazolidin-2-one was dissolved in 10 ml of methylene chloride and treated at room temperature within 30 minutes with a mixture of 2.2 ml of diethylamino-sulfur trifluoride and 5 ml of methylene chloride. After stirring at room temperature for 2 hours the mixture was poured into 50 ml of ice-water and extracted twice with methylene chloride. The organic phase was washed with sodium chloride solution, sodium hydrogen carbonate solution and again with a sodium chloride solution, dried with magnesium sulfate and concentrated. The residue, 0.6 g of yellow honey, was chromatographed on a 30-fold amount of silica gel with methylene chloride-ethyl acetate (19:1) and yielded 80 mg of (RS)-3-[4-(cis-4-fluoro-cyclohexyl)-phenyl]-5-methoxymethyl-oxazolidin-2-one as a colorless oil. 1H-NMR (CDCl3)ppm: 7.47 (d,2H), 7.24 (d,2H), 4.88 (bd,1H), 4.74 (m,1H), 4.04 (t, 1H), 3.91 (m,1H), 3.64 (d,2H), 3.43 (s,3H), 2.53 (m,1H), 2.16 (m,2H), 1.72 (m,6H).

Workup

  1. extractionextracted twice with methylene chloride
  2. washThe organic phase was washed with sodium chloride solution, sodium hydrogen carbonate solution and again with a sodium chloride solution
  3. dry with materialdried with magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue, 0.6 g of yellow honey, was chromatographed on a 30-fold amount of silica gel with methylene chloride-ethyl acetate (19:1)

Sources & evidence

ORD record
ord-743344c08c97402e8d759e98d58f412a
Source dataset
uspto-grants-1996_11
Patent number
US05574055

Reaction notes

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