4-Toluenesulfonyl chloride → HCID 87679671, compound

HRID 899145Notes

Reaction equation

HRID 899145 reaction equation
[Li]CCCC.[CH2:6]([N:13]([CH2:18][CH2:19][OH:20])[C:14]([NH:16][CH3:17])=[O:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH3:21][C:22]1[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1>C1COCC1>[CH2:6]([N:13]([CH2:18][CH2:19][O:20][S:28]([C:25]1[CH:26]=[CH:27][C:22]([CH3:21])=[CH:23][CH:24]=1)(=[O:30])=[O:29])[C:14]([NH:16][CH3:17])=[O:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 69070027HCID 69070027, compoundHCID 178418339Butyllithium

Product 1

HCID 87679671HCID 87679671, compoundYield 48.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

nBuLi (2.8 N, 1.01 g, 0.0157 mol) was added at −78° C. to a solution of 1-benzyl-1-(2-hydroxy-ethyl)-3-methyl-urea (3 g, 0.0143 mol, from (i) above) in 30 ml of dry TBF and stirred at same temperature for 30 min under nitrogen atmosphere. P-Toluenesulfonyl chloride (3 g, 0.0157 mol) in 20 ml of dry THF was added dropwise at −78° C. and stirred for 3 h under nitrogen atmosphere. The reaction was quenched with methanol and solvent evaporated under reduced pressure. The crude was purified by column chromatography over silica gel using 12% methanol in dichloromethane as eluent to yield 2.5 g of the title compound as a solid.

Workup

  1. stirringstirred for 3 h under nitrogen atmosphere
  2. customThe reaction was quenched with methanol and solvent
  3. customevaporated under reduced pressure
  4. customThe crude was purified by column chromatography over silica gel using 12% methanol in dichloromethane as eluent

Sources & evidence

ORD record
ord-c72fb8922eda4a6aaafaa01e8f062f08
Source dataset
uspto-grants-2008_04
Patent number
US07354917B2

Reaction notes

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