p-Toluenesulfonic acid monohydrate → HCID 88402726, compound

HRID 1609054Notes

Reaction equation

HRID 1609054 reaction equation
[NH2:1][C@H:2]1[C@@H:6]([CH3:7])[CH2:5][N:4]([C:8]2[C:17]([F:18])=[CH:16][C:15]3[C:19](=[O:25])[C:20]([C:22]([OH:24])=[O:23])=[CH:21][N:13]4[C:14]=3[C:9]=2[CH2:10][CH2:11][N:12]4[CH3:26])[CH2:3]1.O.[C:28]1([CH3:38])[CH:33]=[CH:32][C:31]([S:34]([OH:37])(=[O:36])=[O:35])=[CH:30][CH:29]=1>C(Cl)(Cl)Cl.CO>[S:34]([C:31]1[CH:32]=[CH:33][C:28]([CH3:38])=[CH:29][CH:30]=1)([OH:37])(=[O:36])=[O:35].[NH2:1][C@H:2]1[C@@H:6]([CH3:7])[CH2:5][N:4]([C:8]2[C:17]([F:18])=[CH:16][C:15]3[C:19](=[O:25])[C:20]([C:22]([OH:24])=[O:23])=[CH:21][N:13]4[C:14]=3[C:9]=2[CH2:10][CH2:11][N:12]4[CH3:26])[CH2:3]1

Participants

5

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 9928823HCID 9928823, compound

Product 1

HCID 88402726HCID 88402726, compoundYield 95.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6212ChloroformSolvent

Procedure

3.2 g of the compound (30) obtained in Example 5 (1) was dissolved in 110 ml of chloroform and 110 ml of methanol, and then 40 ml of methanol solution containing 6.37 g of p-toluenesufonic acid hydrate was added to the solution. The solution was stirred at room temperature for 40 minutes. The solvent was removed by distillation, and the crystal was dispersed in ethanol. The crystal was filtered off and washed successively with ethanol and ether to obtain 4.52 g of crude crystal. The crystal was recrystallized from a mixture solvent of ethanol and water to obtain 4.52 g of the subject compound (78). The result of the analysis of this compound was as follows.

Workup

  1. additionwas added to the solution
  2. customThe solvent was removed by distillation
  3. additionthe crystal was dispersed in ethanol
  4. filtrationThe crystal was filtered off
  5. washwashed successively with ethanol and ether
  6. customto obtain 4.52 g of crude crystal
  7. customThe crystal was recrystallized from a mixture solvent of ethanol and water

Sources & evidence

ORD record
ord-efe2c267a3ee467cacd5945ceddd5744
Source dataset
uspto-grants-1995_03
Patent number
US05399553

Reaction notes

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