Reaction #4563

ord-646e134c4c8349d79582f85770153680

Reaction equation

COC
methylether
COc1ccc(C[C@H]2C(=O)N[C@H](C)C(=O)N(C)[C@@H]3Cc4ccc(cc4)Oc4cc(ccc4O)C[C@H](C(=O)N[C@@H](C)C(=O)N[C@@H](C)C(=O)N2C)N(C)C3=O)cc1.COc1ccc(C[C@H]2C(=O)N[C@H](C)C(=O)N(C)[C@@H]3Cc4ccc(cc4)Oc4cc(ccc4O)C[C@H](C(=O)N[C@@H](C)C(=O)N[C@@H](C)C(=O)N2C)N(C)C3=O)cc1.COc1ccc(C[C@H]2C(=O)N[C@H](C)C(=O)N(C)[C@@H]3Cc4ccc(cc4)Oc4cc(ccc4O)C[C@H](C(=O)N[C@@H](C)C(=O)N[C@@H](C)C(=O)N2C)N(C)C3=O)cc1.COc1ccc(C[C@H]2C(=O)N[C@H](C)C(=O)N(C)[C@@H]3Cc4ccc(cc4)Oc4cc(ccc4O)C[C@H](C(=O)N[C@@H](C)C(=O)N[C@@H](C)C(=O)N2C)N(C)C3=O)cc1.O.O.O.O.O
TPC-A
CI
methyl iodide
→
COc1ccc(C[C@H]2C(=O)N[C@@H](C)C(=O)N(C)[C@H]3Cc4ccc(cc4)Oc4cc(ccc4OC)C[C@@H](C(=O)N[C@H](C)C(=O)N[C@@H](C)C(=O)N2C)N(C)C3=O)cc1
methylether of TPC-A

Reactants

COC
methylether
COc1ccc(C[C@H]2C(=O)N[C@H](C)C(=O)N(C)[C@@H]3Cc4ccc(cc4)Oc4cc(ccc4O)C[C@H](C(=O)N[C@@H](C)C(=O)N[C@@H](C)C(=O)N2C)N(C)C3=O)cc1.COc1ccc(C[C@H]2C(=O)N[C@H](C)C(=O)N(C)[C@@H]3Cc4ccc(cc4)Oc4cc(ccc4O)C[C@H](C(=O)N[C@@H](C)C(=O)N[C@@H](C)C(=O)N2C)N(C)C3=O)cc1.COc1ccc(C[C@H]2C(=O)N[C@H](C)C(=O)N(C)[C@@H]3Cc4ccc(cc4)Oc4cc(ccc4O)C[C@H](C(=O)N[C@@H](C)C(=O)N[C@@H](C)C(=O)N2C)N(C)C3=O)cc1.COc1ccc(C[C@H]2C(=O)N[C@H](C)C(=O)N(C)[C@@H]3Cc4ccc(cc4)Oc4cc(ccc4O)C[C@H](C(=O)N[C@@H](C)C(=O)N[C@@H](C)C(=O)N2C)N(C)C3=O)cc1.O.O.O.O.O
TPC-A
—
potassium fluoride alumina
CI
methyl iodide

Reagents

None

Solvents

COCCOC
1,2-dimethoxy ethane

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherAfter completion of the reaction
  2. 2
    Filtrationthe solution was filtered
  3. 3
    workup.DISTILLATIONthe filtrate was subjected to distillation in vacuo
  4. 4
    Otherto remove solvent
  5. 5
    Otherthe residue obtained
  6. 6
    Otherwas purified by P-TLC
  7. 7
    Otherfollowed by the recrystallization from methanol

Procedure

In 10 ml of anhydrous 1,2-dimethoxy ethane, 100 mg of the methylether derivative of TPC-A was dissolved and 240 mg of potassium fluoride-alumina and excess amount of methyl iodide were added and the mixture was shielded from the light while stirring at room temperature overnight. After completion of the reaction, the solution was filtered, the filtrate was subjected to distillation in vacuo to remove solvent and the residue obtained was purified by P-TLC followed by the recrystallization from methanol to obtain N-methyl derivative of the methylether of TPC-A (98 mg) as colorless crystal having m.p. of 285° to 292° C. (decomp) and [α]D27 of -166° (CHCl3).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04725578uspto-grants-1988_02