4-Methoxybenzenesulfonyl chloride → HCID 86585804, compound

HRID 2271010Notes

Reaction equation

HRID 2271010 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[CH:5][CH:4]=1.Cl.[CH2:14]([O:21][NH:22][C:23]([C@H:25]1[C@@H:30]([CH3:31])[N:29]([S:32]([CH3:35])(=[O:34])=[O:33])[CH2:28][CH2:27][NH:26]1)=[O:24])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>O1CCOCC1.N1C=CC=CC=1>[CH2:14]([O:21][NH:22][C:23]([C@H:25]1[C@@H:30]([CH3:31])[N:29]([S:32]([CH3:35])(=[O:33])=[O:34])[CH2:28][CH2:27][N:26]1[S:9]([C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)(=[O:11])=[O:10])=[O:24])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 2

HCID 74014-Methoxybenzenesulfonyl chloride3×HCID 86585805HCID 86585805, compound

Product 1

HCID 86585804HCID 86585804, compoundYield 99.8%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 312751,4-DioxaneSolvent3×

Procedure

A solution of 4-methoxybenzenesulfonyl chloride (284 mg) in dioxane (2 ml) was added to a solution of (2R,3R)-N-benzyloxy-4-methanesulfonyl-3-methyl-2-piperazinecarboxamide hydrochloride (200 mg) in pyridine (2 ml) with cooling on an ice bath. The mixture was stirred at ambient temperature for 3.5 hours. 4-Methoxybenzene-sulfonyl chloride (60 mg) in dioxane (1 ml) was added thereto, and the mixture was stirred at ambient temperature for 2 hours. 4-Methoxybenzenesulfonyl chloride (60 mg) in dioxane (1 ml) was added to the mixture. The reaction mixture was stirred at ambient temperature for 2 hours, and the reaction was quenched by adding 3-(N,N-dimethyl-amino)propylamine (0.1 ml). The mixture was partitioned between 0.6N HCl and AcOEt. The organic layer was washed with 0.6N HCl, saturated aqueous NaHCO3 solution and saturated aqueous NaCl solution, dried over MgSO4 and concentrated in vacuo. The residue was purified by SiO2 column chromatography (eluent: AcOEt in n-hexane 60% to 80%) to give 273 mg of (2R,3R)-N-benzyloxy-4-methanesulfonyl-1-(4-methoxy-benzenesulfonyl)-3-methyl-2-piperazinecarboxamide as an amorphous powder.

Workup

  1. temperaturewith cooling on an ice bath
  2. stirringthe mixture was stirred at ambient temperature for 2 hours
  3. stirringThe reaction mixture was stirred at ambient temperature for 2 hours
  4. customthe reaction was quenched
  5. additionby adding 3-(N,N-dimethyl-amino)propylamine (0.1 ml)
  6. customThe mixture was partitioned between 0.6N HCl and AcOEt
  7. washThe organic layer was washed with 0.6N HCl, saturated aqueous NaHCO3 solution and saturated aqueous NaCl solution
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by SiO2 column chromatography (eluent: AcOEt in n-hexane 60% to 80%)

Sources & evidence

ORD record
ord-9a82b48dec1b4487a6c513d436bbee08
Source dataset
uspto-grants-2001_12
Patent number
US06333324B1

Reaction notes

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