Sodium Methoxide → HCID 23368635, compound

HRID 1608844Notes

Reaction equation

HRID 1608844 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:33])[C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[N:16]([CH:27]([C:29]([O:31][CH3:32])=[O:30])[CH3:28])[S:17]([C:20]1[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=1)(=[O:19])=[O:18].C[O-].[Na+]>CN(C=O)C>[Cl:15][C:13]1[CH:14]=[C:9]2[C:10](=[CH:11][CH:12]=1)[N:16]([S:17]([C:20]1[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=1)(=[O:19])=[O:18])[C:27]([CH3:28])([C:29]([O:31][CH3:32])=[O:30])[C:8]2([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1])[OH:33]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 18997483HCID 18997483, compound

Product 1

HCID 23368635HCID 23368635, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture containing 0.5 g of 2',5-dichloro- 2-[N-(1-methoxycarbonylethyl)-N-(tosyl)amino]benzophenone, 0.1 g of sodium methylate and 2 ml of DMF is stirred for 20 hours at room temperature under nitrogen. It is concentrated under vacuum, the residue is taken up with water and the precipitate is filtered off and washed with water. The residue is chromatographed on silica using DCM as the eluent to give 60 mg of the cis isomer and 250 mg of the trans isomer.

Workup

  1. concentrationIt is concentrated under vacuum
  2. filtrationthe precipitate is filtered off
  3. washwashed with water
  4. customThe residue is chromatographed on silica
  5. customto give 60 mg of the cis isomer and 250 mg of the trans isomer

Sources & evidence

ORD record
ord-49c59175be4540a6b88d520d52f15bc5
Source dataset
uspto-grants-1995_03
Patent number
US05397801

Reaction notes

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