Sodium Methoxide → Beciparcil

HRID 5995Notes

Reaction equation

HRID 5995 reaction equation
C([O:4][C@@H:5]1[C@@H:19]([O:20]C(=O)C)[C@H:18]([O:24]C(=O)C)[CH2:17][S:16][C@H:6]1[S:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][CH:9]=1)(=O)C.C[O-].[Na+]>CO>[S:7]([C:8]1[CH:9]=[CH:10][C:11]([C:14]#[N:15])=[CH:12][CH:13]=1)[C@@H:6]1[S:16][CH2:17][C@@H:18]([OH:24])[C@H:19]([OH:20])[C@H:5]1[OH:4]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 147953324-cyanophenyl 2,3,4-tri-O-acetyl-1,5-dithio-beta-D-xylopyranoside

Product 1

HCID 71788BeciparcilYield 89.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Under a nitrogen atmosphere, 8.5 g (21.10-3 mol) of 4-cyanophenyl 2,3,4-tri-O-acetyl-1,5-dithio-β-D-xylopyranoside (Example 1a) are suspended in 100 ml of methanol, and 2 ml of sodium methylate (8% w/v of Na in methanol) are then added. The reaction medium is stirred at room temperature until the starting material has completely dissolved (2 hours) and is then neutralized by the addition of Amberlite® IR 120 H+ resin. The methanol is evaporated off under reduced pressure; the crude product obtained is recrystallized from an ethanol/water mixture (65/25 v/v) to give 5.3 g (yield: 89.7%) of the expected product.

Workup

  1. dissolutionhas completely dissolved (2 hours)
  2. additionis then neutralized by the addition of Amberlite® IR 120 H+ resin
  3. customThe methanol is evaporated off under reduced pressure
  4. customthe crude product obtained
  5. customis recrystallized from an ethanol/water mixture (65/25 v/v)

Sources & evidence

ORD record
ord-df939d720ab54ac1ba13f03f130484a8
Source dataset
uspto-grants-1993_09
Patent number
US05246961

Reaction notes

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