Sodium Methoxide → HCID 178459240, compound

HRID 237340Notes

Reaction equation

HRID 237340 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:14]3[C:10](=[N:11][N:12]=[C:13]3[C@H:15]3[CH2:20][CH2:19][C@H:18]([O:21][CH:22]([CH3:24])[CH3:23])[CH2:17][CH2:16]3)[CH2:9][N:8]([C:25](=[O:31])[CH2:26][O:27]C(=O)C)[CH2:7][C:6]=2[CH:32]=1.C[O-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:14]3[C:10](=[N:11][N:12]=[C:13]3[C@H:15]3[CH2:20][CH2:19][C@H:18]([O:21][CH:22]([CH3:24])[CH3:23])[CH2:17][CH2:16]3)[CH2:9][N:8]([C:25](=[O:31])[CH2:26][OH:27])[CH2:7][C:6]=2[CH:32]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 178476475HCID 178476475, compound

Product 1

HCID 178459240HCID 178459240, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of trans-acetic acid 2-[8-chloro-1-(4-isopropoxy-cyclohexyl)-4H,6H-2,3,5,10b-tetraaza-benzoazulen-5-yl]-2-oxo-ethyl ester in methanol (5 ml) was added one drop of a 30% methanolic sodium methoxide solution at room temperature. Stirring for 40 minutes was followed by quenching with water. The mixture was extracted with three portions of tert-butyl methyl ether. The combined org layers were dried over anhydrous sodium sulfate and concentrated in vacuo. Flash-chromatography with n-heptane/2-propanol as eluent gave the title compound (0.033 g, 49%) as white solid. MS m/e: 419 (M+H+).

Workup

  1. customby quenching with water
  2. extractionThe mixture was extracted with three portions of tert-butyl methyl ether
  3. dry with materialThe combined org layers were dried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-93de254beefd4f64a98332d9126ae490
Source dataset
uspto-grants-2014_02
Patent number
US08642590B2

Reaction notes

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