Methanol → HCID 22898587, compound

HRID 1018494Notes

Reaction equation

HRID 1018494 reaction equation
[CH3:1][CH:2]([NH:8][C:9]1[CH:18]=[N:17][C:16]2[C:11](=[CH:12][C:13]([O:21][CH3:22])=[C:14]([O:19][CH3:20])[CH:15]=2)[N:10]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].C[OH:24]>>[CH3:20][O:19][C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][C:13]=1[O:21][CH3:22])[N:10]=[C:9]([NH:8][C@@H:2]1[CH2:1][C@@H:6]3[CH2:7][C@H:3]1[CH2:4][C@H:5]3[OH:24])[CH:18]=[N:17]2

Participants

3

Reactant 2

HCID 887MethanolHCID 54383944HCID 54383944, compound

Product 1

HCID 22898587HCID 22898587, compound

Conditions

Temperature
22 °C

Procedure

The fungi is stored at −25° C. 250 mL conical flasks each containing 50 mL seed culture medium (medium 216) are inoculated with 2 mL of fungi suspension and incubated on a rotary shaker (200 rpm at 23° C. for 3 days. 250 mL conical flasks each containing 50 mL of the same medium were inoculated with mL of the seed culture and incubated on a rotary shaker (200 rpm ) at 23° C. After 24 hours, (1R,2R,4)- (+)-Bicyclo[2.2.]hept-2-yl-(6,7-dimethoxyquinoxalin-2-yl)-amine of Example 25 is dissolved in MeOH added to the flasks to a final concentration of 300 mg/L. The cultures are harvested after 24 hours of incubation. (Medium 216: Glucose 0.4%, Yeast extract 0.05%, Soya flour 0.05%, NaCI 0.05%, KH2PO4 0.05.) The extraction is performed using 2 volumes of acetonitrile, 1 volume de tert-butylmethyl ether and volume of n-heptane were added to 1 volume of broth. After magnetic stirring at 22° C, the extract separates to 3 layers. The intermediate layer is collected and evaporated to dryness, and redissolved in ethyl acetate. The ethyl acetate extract is separated on silica gel (0.04-0.063 mm) using ethyl acetate as eluent. Fractions containing the biotransformation product are separated on C1 8 silica using a H2O/MeOH gradient as eluent. This chromatography yields the pure titled compound as an amorphous yellow powder, m.p. 190-192° C.

Workup

  1. customis stored at −25° C
  2. custom250 mL conical flasks each containing 50 mL seed culture medium (medium 216) are inoculated with 2 mL of fungi suspension
  3. customat 23° C.
  4. customfor 3 days
  5. custom250 mL conical flasks each containing 50 mL of the same medium were inoculated with mL of the seed culture
  6. customincubated on a rotary shaker (200 rpm ) at 23° C
  7. additionadded to the flasks to a final concentration of 300 mg/L
  8. waitThe cultures are harvested after 24 hours of incubation
  9. extraction(Medium 216: Glucose 0.4%, Yeast extract 0.05%, Soya flour 0.05%, NaCI 0.05%, KH2PO4 0.05.)
  10. extractionThe extraction
  11. additionwere added to 1 volume of broth
  12. customThe intermediate layer is collected
  13. customevaporated to dryness
  14. dissolutionredissolved in ethyl acetate
  15. extractionThe ethyl acetate extract
  16. customis separated on silica gel (0.04-0.063 mm)
  17. additionFractions containing the biotransformation product
  18. customare separated on C1 8 silica using a H2O/MeOH gradient as eluent

Sources & evidence

ORD record
ord-9175dc75e13246a1ad2edce06aa5914d
Source dataset
uspto-grants-2002_11
Patent number
US06482834B2

Reaction notes

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