Pyridine → HCID 19828474, compound

HRID 1494527Notes

Reaction equation

HRID 1494527 reaction equation
[CH3:1][C:2]1[C:7]([OH:8])=[C:6]([CH2:9][OH:10])[C:5]([CH:11]([O:19]C(=O)C)[C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)=[CH:4][N:3]=1.[C:23]1([CH3:33])[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1.N1C=CC=CC=1>C(Cl)Cl>[CH3:1][C:2]1[C:7]([OH:8])=[C:6]([CH2:9][O:10][S:29]([C:26]2[CH:27]=[CH:28][C:23]([CH3:33])=[CH:24][CH:25]=2)(=[O:31])=[O:30])[C:5]([CH:11]([OH:19])[C:12]2[CH:13]=[CH:14][C:15]([Cl:18])=[CH:16][CH:17]=2)=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 19828471HCID 19828471, compound

Product 1

HCID 19828474HCID 19828474, compoundYield 59.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.24 g (0.66 mmole) of (+)-2-methyl-3-hydroxy-4- hydroxymethyl-5-[4-chloro-α-acetoxybenzyl]pyridine are poured into a 25 ml round bottomed flask and dissolved in 10 ml of methylene chloride. 190 mg (1 mmole) of p-toluene sulphonyl chloride and 75 mg (1 mmole) of pyridine are then added. The reaction mixture is stirred at room temperature for 18 hours the solvent is then removed under reduced pressure. 5 ml of methanolic ammonia are added and the mixture is stirred at room temperature for 2 hours. The solvent is removed under vacuum, dissolved again in 1 ml of methanol and purified by silica TLC. 170 mg of the title compound were obtained as an off-white solid.

Workup

  1. customis then removed under reduced pressure
  2. addition5 ml of methanolic ammonia are added
  3. stirringthe mixture is stirred at room temperature for 2 hours
  4. customThe solvent is removed under vacuum
  5. dissolutiondissolved again in 1 ml of methanol
  6. custompurified by silica TLC

Sources & evidence

ORD record
ord-09bc0596081b45338ba0fc08adbcc080
Source dataset
uspto-grants-1991_06
Patent number
US05026855

Reaction notes

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