Water → HCID 70055700, compound

HRID 583320Notes

Reaction equation

HRID 583320 reaction equation
[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[C:6]([CH3:11])[C:5]=1[NH:12][S:13]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1)(=[O:15])=[O:14].[H-].[Na+].[CH3:27][O:28][C:29]1[CH:30]=[C:31]([CH:34]=[CH:35][CH:36]=1)[CH2:32]Cl.O>CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[C:6]([CH3:11])[C:5]=1[N:12]([S:13]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1)(=[O:15])=[O:14])[CH2:32][C:31]1[CH:34]=[CH:35][CH:36]=[C:29]([O:28][CH3:27])[CH:30]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 699943-Methoxybenzyl chlorideHCID 53963569HCID 53963569, compound

Product 1

HCID 70055700HCID 70055700, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.699 g (2.0 mmol) of the product of Example 62 in 5 mL of DMF was added 0.096 g (2.4 mmol) of 60% sodium hydride. The resulting mixture was stirred for 30 min at room temperature and then 0.376 g (2.4 mmol) of m-methoxybenzyl chloride and 0.089 g (0.24 mmol) of tetrabutylammonium iodide were added. The reaction mixure was stirred for 18 hr at room temperature, poured into water and then extracted with ether. The combined organics were washed with water and brine, dried over MgSO4, filtered and concentad in vacuo. The crude solid was triturated with hexane to provide 0.768 g (82%) of the desired product as white solid. Electrospray Mass Spec 470.3 (M+H).

Workup

  1. stirringThe reaction mixure was stirred for 18 hr at room temperature
  2. extractionextracted with ether
  3. washThe combined organics were washed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customThe crude solid was triturated with hexane

Sources & evidence

ORD record
ord-3f7410b6ece84b2c9da6fc2068772de3
Source dataset
uspto-grants-1999_07
Patent number
US05929097

Reaction notes

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