Dichloromethane → Marcfortine B

HRID 1955612Notes

Reaction equation

HRID 1955612 reaction equation
[CH3:1][C:2]1([CH3:35])[O:34][C:7]2[CH:8]=[CH:9][C:10]3[C@@:15]4([C:27]([CH3:29])([CH3:28])[C@@H:26]5[C@@:17]6([N:32](C)[C:30](=[O:31])[C@:24]7([CH2:25]5)[N:19]([CH2:20][CH2:21][CH2:22][CH2:23]7)[CH2:18]6)[CH2:16]4)[C:13](=[O:14])[NH:12][C:11]=3[C:6]=2[O:5][CH:4]=[CH:3]1.C(Cl)Cl>CN(C=O)C>[CH3:1][C:2]1([CH3:35])[O:34][C:7]2[CH:8]=[CH:9][C:10]3[C@@:15]4([C:27]([CH3:28])([CH3:29])[C@H:26]5[C@@:17]6([NH:32][C:30](=[O:31])[C@:24]7([CH2:25]5)[N:19]([CH2:20][CH2:21][CH2:22][CH2:23]7)[CH2:18]6)[CH2:16]4)[C:13](=[O:14])[NH:12][C:11]=3[C:6]=2[O:5][CH:4]=[CH:3]1

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 15385507HCID 15385507, compound

Product 1

HCID 102091744Marcfortine B

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
28 °C

Procedure

The contents of 100 flasks, each containing 100 ml fermentation as described in the protocol for biotransformation and which had been shaken at 28° C. for 24-72 hours following addition of Marcfortine A (0.010 g per flask, 1 g total) in DMF (0.2 ml per flask, 20 ml total) are each treated with CH2Cl2 (100 ml). The contents are combined and stirred in a waring blender for 5 minutes. The mixture is centrifuged and the resulting aqueous layer is decanted. The organic layer is collected, dried (sodium sulfate), filtered and concentrated. The components of the crude mixture are separated by a series of column chromatographies using a silica gel--solid extract ratio of 50-125:1. Columns are eluted with either 2-5% methanol in CH2Cl2 or 15-60% acetone in C2Cl2. From these chomatographic separations there is isolated Marcfortine B. HRMS (FAB); mle, found, 464.2563; calculated for C27H33N3O4 +H1, 464.2549.

Workup

  1. stirringstirred in a waring blender for 5 minutes
  2. customthe resulting aqueous layer is decanted
  3. customThe organic layer is collected
  4. dry with materialdried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe components of the crude mixture are separated by a series of column chromatographies
  8. extractionsolid extract ratio of 50-125:1
  9. washColumns are eluted with either 2-5% methanol in CH2Cl2 or 15-60% acetone in C2Cl2

Sources & evidence

ORD record
ord-1fdfde1ef9e34727b5befd667500b58b
Source dataset
uspto-grants-1998_07
Patent number
US05776936

Reaction notes

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