Water → HCID 54233451, compound

HRID 2227477Notes

Reaction equation

HRID 2227477 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[C:12]([NH:21][C:22]([NH2:24])=S)[CH:13]=[CH:14][C:15]=1[N:16]1[CH:20]=[CH:19][CH:18]=[N:17]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(C)C=CC(S(Cl)(=O)=O)=CC=1.N1C=CC=CC=1.O>C(Cl)Cl>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][C:10]1[CH:11]=[C:12]([NH:21][C:22]#[N:24])[CH:13]=[CH:14][C:15]=1[N:16]1[CH:20]=[CH:19][CH:18]=[N:17]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 18474028HCID 18474028, compound

Product 1

HCID 54233451HCID 54233451, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of the compound (315 mg) obtained in Example 2c, p-toluenesulfonyl chloride (190 mg) and pyridine (2 ml) was stirred at room temperature for 70 minutes. Water was added to the reaction mixture and extraction with methylene chloride was conducted. The organic layer was washed with brine, dried with anhydrous sodium sulfate and then concentrated at reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent; ethyl acetate:n-hexane=1:1) to give the titled compound (yield, 87%).

Workup

  1. washThe organic layer was washed with brine
  2. dry with materialdried with anhydrous sodium sulfate
  3. concentrationconcentrated at reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (eluent; ethyl acetate:n-hexane=1:1)

Sources & evidence

ORD record
ord-ad1d8ba3748349f28529409b9570ff11
Source dataset
uspto-grants-2002_07
Patent number
US06414005B1

Reaction notes

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