HCID 11222326, compound → HCID 10173120, compound

HRID 1268981Notes

Reaction equation

HRID 1268981 reaction equation
[O:1]=[S:2]1(=[O:25])[CH2:7][CH:6]=[C:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:18][C@H:17]([CH2:19][N:20]=[N+:21]=[N-:22])[O:16][C:15]3=[O:23])=[CH:10][C:9]=2[F:24])[CH2:4][CH2:3]1.[F:26][C:27](S(=O)(=O)C1C=CC=CC=1)=[CH2:28]>C1(C)C=CC=CC=1.ClCCl>[O:25]=[S:2]1(=[O:1])[CH2:3][CH:4]=[C:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:18][C@H:17]([CH2:19][N:20]4[CH:28]=[C:27]([F:26])[N:22]=[N:21]4)[O:16][C:15]3=[O:23])=[CH:10][C:9]=2[F:24])[CH2:6][CH2:7]1

Participants

5

Reactant 2

HCID 11222326HCID 11222326, compoundHCID 13866134HCID 13866134, compound

Product 1

HCID 10173120HCID 10173120, compoundYield 4%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

(5R)-3-[4-(1,1-Dioxo-3,6-dihydro-2H-thiopyran-4-yl)-3-fluorophenyl]-5-(azidomethyl)-oxazolidin-2-one (Reference Example 2) (0.7 g, 1.9 mmol) and (1-fluoroethenyl)-phenylsulfane dioxide (0.7 g, 3.8 mmol) (D. P. Mathews and J. R. McCarthy, JOC 55 (9), 1990, p 2973) were suspended/dissolved in toluene (5 ml) and heated to reflux under stirring for 2 days. The reaction mixture was cooled to room temperature, diluted with dichloromethane, washed with phosphate buffer (pH 7) and dried over sodium sulfate. Chromatography on silica gel with hexanes/acetone (1:1) gave 28 mg (4%) of the title compound as a colourless solid (Rf ˜0.25, TLC:hexanes/acetone, 1:1). The major product was the corresponding 5-fluoro-1,2,3-triazoyl compound with an Rf of ˜0.2.

Workup

  1. temperatureheated
  2. temperatureto reflux
  3. washwashed with phosphate buffer (pH 7)
  4. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-289e1c148e9745a08efa51e40d9f2396
Source dataset
uspto-grants-2007_04
Patent number
US07199143B2

Reaction notes

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