Methanol → HCID 57179421, compound

HRID 1742438

Reaction equation

HRID 1742438 reaction equation
[CH2:1]([C:3]([CH2:22][CH3:23])([P:18]([OH:21])([OH:20])=[O:19])[C@H:4]1[CH2:13][CH2:12][C@@H:11]2[C@@H:6]([CH2:7][CH2:8][N:9]([C:14]([O:16][CH3:17])=[O:15])[CH2:10]2)[CH2:5]1)[CH3:2].[CH3:24][OH:25]>C1(C)C=CC(S([O-])(=O)=O)=CC=1.C([N+](CC)(CC)CC)C>[CH2:22]([C:3]([CH2:1][CH3:2])([P:18]([OH:20])([OH:21])=[O:19])[CH:4]1[CH2:13][CH2:12][CH:11]2[CH:6]([CH2:7][CH:8]([O:25][CH3:24])[N:9]([C:14]([O:16][CH3:17])=[O:15])[CH2:10]2)[CH2:5]1)[CH3:23]

Participants

4

Reactant 2

HCID 887Methanol3×HCID 67845082HCID 67845082, compound

Product 1

HCID 57179421HCID 57179421, compound

Reagents, catalysts & solvents 1

HCID 101846Tetraethylammonium p-toluenesulphonateCatalyst

Procedure

Four carbon plate electrodes were immersed into a solution containing the compound from Example 1 (250 mg), tetraethylammonium p-toluenesulfonate (21 mg), in methanol (10 ml). A constant current of 0.5 A was applied to the electrodes. Additional methanol (7.8 ml) was added to the reaction to replace methanol which was lost due to evaporation. After 550 coulombs of current had passed, the electrodes were removed and the solution was added to 10% brine. This mixture was extracted with ether (3×15 ml). The combined ether extracts were washed with water and with brine, dried over magnesium sulfate, and concentrated in vacuo at room temperature to give 237 ml of the title compound as an oil. The material was stored in the refrigerator and used in the next step without further purification.

Workup

  1. customwas lost due to evaporation
  2. customthe electrodes were removed
  3. additionthe solution was added to 10% brine
  4. extractionThis mixture was extracted with ether (3×15 ml)
  5. washThe combined ether extracts were washed with water and with brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo at room temperature

Sources & evidence

ORD record
ord-6996d2f68cf74cfcb88ed919b8745fdb
Source dataset
uspto-grants-1994_08
Patent number
US05338851

Linked notes

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