4-Toluenesulfonyl chloride → N-((5S)-3-(4(1-p-Toluenesulfonyl-1,2,5,6-tetrahydropyrid-4-yl)phenyl)2-oxooxazolidin-5-ylmethyl)acetamide

HRID 650279Notes

Reaction equation

HRID 650279 reaction equation
C(N(CC)CC)C.[C:8]1([CH3:18])[CH:13]=[CH:12][C:11]([S:14](Cl)(=[O:16])=[O:15])=[CH:10][CH:9]=1.[NH:19]1[CH2:24][CH2:23][C:22]([C:25]2[CH:30]=[CH:29][C:28]([N:31]3[CH2:35][C@H:34]([CH2:36][NH:37][C:38](=[O:40])[CH3:39])[O:33][C:32]3=[O:41])=[CH:27][CH:26]=2)=[CH:21][CH2:20]1>ClCCl>[C:8]1([CH3:18])[CH:13]=[CH:12][C:11]([S:14]([N:19]2[CH2:24][CH2:23][C:22]([C:25]3[CH:30]=[CH:29][C:28]([N:31]4[CH2:35][C@H:34]([CH2:36][NH:37][C:38](=[O:40])[CH3:39])[O:33][C:32]4=[O:41])=[CH:27][CH:26]=3)=[CH:21][CH2:20]2)(=[O:16])=[O:15])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 20638827N-((5S)-3-(4-(1,2,5,6-tetrahydropyrid-4-yl)phenyl)-2-oxooxazolidin-5-ylmethyl)acetamide

Product 1

HCID 20598823N-((5S)-3-(4(1-p-Toluenesulfonyl-1,2,5,6-tetrahydropyrid-4-yl)phenyl)2-oxooxazolidin-5-ylmethyl)acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (202 mg), followed by p-toluenesulfonyl chloride (171 mg) were added to a stirred suspension of the TFA salt of Example 2 (322 mg) in dichloromethane (10 ml). After stirring for 30 minutes at ambient temperature, the reaction mixture had become a solution and the reaction was complete. The solution was washed with 2N HCl, water, saturated NaHCO3 and saturated NaCl. The organic phase was dried over anhydrous Na2SO4 and evaporated to give a crystalline solid which was triturated with ether to give the title compound. Yield=306 mg, 87%.

Workup

  1. washThe solution was washed with 2N HCl, water, saturated NaHCO3 and saturated NaCl
  2. dry with materialThe organic phase was dried over anhydrous Na2SO4
  3. customevaporated
  4. customto give a crystalline solid which
  5. customwas triturated with ether

Sources & evidence

ORD record
ord-e17acdb829fd40e8be2ce4383dd66667
Source dataset
uspto-grants-2001_08
Patent number
US06271383B1

Reaction notes

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