23477-98-7 → Lankacidin C

HRID 2072866Notes

Reaction equation

HRID 2072866 reaction equation
[CH3:1][CH:2]1[C:18](=[O:19])[C:17]2([CH3:23])[C:20]([O:22][CH:3]1[CH2:4][CH:5]([O:33]C(C)=O)[CH:6]=[CH:7][C:8]([CH3:32])=[CH:9][CH2:10][CH:11]([OH:31])[CH:12]=[CH:13][C:14]([CH3:30])=[CH:15][CH:16]2[NH:24][C:25]([C:27]([CH3:29])=[O:28])=[O:26])=[O:21]>CO>[CH3:1][C@H:2]1[C:18](=[O:19])[C@@:17]2([CH3:23])[C:20]([O:22][C@@H:3]1[CH2:4][C@H:5]([OH:33])[CH:6]=[CH:7][C:8]([CH3:32])=[CH:9][CH2:10][C@H:11]([OH:31])[CH:12]=[CH:13][C:14]([CH3:30])=[CH:15][C@H:16]2[NH:24][C:25]([C:27]([CH3:29])=[O:28])=[O:26])=[O:21]

Participants

3

Reactant 1

HCID 538256723477-98-7

Product 1

HCID 6440871Lankacidin CYield 26.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 20 ml of methanol was dissolved 102 mg of lankacidin A. To the solution was added a 80 ml aqueous solution of 2.0 g of the enzyme prepared in Reference Example 11. The mixture was stirred at room temperature for 35 minutes, then methanol was distilled off. The residue was extracted with methyl isobutyl ketone-tetrahydrofuran (1:1). The extract was dried on MgSO4, then the solvent was distilled off. To the residue was added ether to give a white powdery crystalline substance, which was collected by filtration and dried to obtain 24.85 mg of the title compound. This product was in agreement with lankacidin C obtained by a fermentative method in NMR, IR and TLC.

Workup

  1. customprepared in Reference Example 11
  2. distillationmethanol was distilled off
  3. extractionThe residue was extracted with methyl isobutyl ketone-tetrahydrofuran (1:1)
  4. customThe extract was dried on MgSO4
  5. distillationthe solvent was distilled off
  6. additionTo the residue was added ether
  7. customto give a white powdery crystalline substance, which
  8. filtrationwas collected by filtration
  9. customdried

Sources & evidence

ORD record
ord-16740897f5a7466c985f21d2a984423f
Source dataset
uspto-grants-1990_04
Patent number
US04914206

Reaction notes

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