Methyl p-toluenesulfonate → HCID 86749914, compound

HRID 864507Notes

Reaction equation

HRID 864507 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:10][C@H:9]3[C@@H:11]([O:21][CH2:22][O:23][CH3:24])[C@H:12]([O:17][CH2:18][O:19][CH3:20])[C@@H:13]([CH2:15][OH:16])[O:14][C@H:8]3[N:7]([CH2:25][CH2:26][N:27]([CH2:30][CH3:31])[CH2:28][CH3:29])[C:6]=2[CH:32]=1.O1CCC[CH2:34]1.CN(C)C=O.[H-].[Na+].C1(C)C=CC(S(OC)(=O)=O)=CC=1>O.CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:10][C@H:9]3[C@@H:11]([O:21][CH2:22][O:23][CH3:24])[C@H:12]([O:17][CH2:18][O:19][CH3:20])[C@@H:13]([CH2:15][O:16][CH3:34])[O:14][C@H:8]3[N:7]([CH2:25][CH2:26][N:27]([CH2:28][CH3:29])[CH2:30][CH3:31])[C:6]=2[CH:32]=1

Participants

7

Reactant 4

HCID 6645Methyl p-toluenesulfonateHCID 24758Sodium hydrideHCID 21974620tetrahydrofuran N,N-dimethylformamideHCID 86749912HCID 86749912, compound

Product 1

HCID 86749914HCID 86749914, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To the solution of 92 mg of the compound (25) obtained in Example 24 in 4.5 ml of a mixed solution of tetrahydrofuran-dimethylformamide (2:1), 30 mg of sodium hydride and 80 μl of methyl p-toluenesulfonate were added, and the mixture was stirred for five hours. After methanol was added to the solution, the mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with water, and saturated aqueous sodium chloride successively and was dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The resulting residue was purified by silica gel column chromatography, and the title compound was obtained from the fraction of chloroformmethanol (19:1).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water, and saturated aqueous sodium chloride successively
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ce131277364049298b3a0f249f48cd68
Source dataset
uspto-grants-1996_10
Patent number
US05563137

Reaction notes

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