Disoxaril → 5-{7-[4-(4,5-Dihydro-2-oxazolyl)phenoxy]heptyl}-3-isoxazolemethanol

HRID 359815Notes

Reaction equation

HRID 359815 reaction equation
[O:1]1[CH2:5][CH2:4][N:3]=[C:2]1[C:6]1[CH:25]=[CH:24][C:9]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]2[O:22][N:21]=[C:20]([CH3:23])[CH:19]=2)=[CH:8][CH:7]=1.[O:26]=C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O>>[O:1]1[CH2:5][CH2:4][N:3]=[C:2]1[C:6]1[CH:7]=[CH:8][C:9]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]2[O:22][N:21]=[C:20]([CH2:23][OH:26])[CH:19]=2)=[CH:24][CH:25]=1

Participants

3

Reactant 2

HCID 55717DisoxarilHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

Product 1

HCID 200641495-{7-[4-(4,5-Dihydro-2-oxazolyl)phenoxy]heptyl}-3-isoxazolemethanol

Procedure

5-{7-[4-(4,5-Dihydro-2-oxazolyl)phenoxy]heptyl}-3-methylisoxazole (Example 1c) (1 g) was added to each of three 10-liter fermentation tanks containing a culture of Aspergillus niger (A1) in soy-dextrose medium. After 24 hours, thin layer chromatography showed essentially complete conversion to a more polar product. The total fermentation brews were extracted with two volumes each of dichloromethane. These were combined and concentrated in vacuo. The concentrate was washed with 0.05N sodium hydroxide and with water, leaving an oily material upon removal of remaining solvent. Several crystallizations from ethyl acetate and from acetone yielded 330 mg of 5-{7-[4-(4,5-dihydro-2-oxazolyl)phenoxy]heptyl}-3-isoxazolemethanol, colorless needles, m.p. 122°-124° C. The structure was established by nmr, ir and uv spectra.

Workup

  1. extractionThe total fermentation brews were extracted with two volumes each of dichloromethane
  2. concentrationconcentrated in vacuo
  3. washThe concentrate was washed with 0.05N sodium hydroxide and with water
  4. customleaving an oily material
  5. customupon removal of remaining solvent
  6. customSeveral crystallizations from ethyl acetate

Sources & evidence

ORD record
ord-88e3f8cc1d86468f97250d55e328c2c8
Source dataset
uspto-grants-1991_03
Patent number
US05002960

Reaction notes

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