p-Toluenesulfonic acid → HCID 14053130, compound

HRID 1646504Notes

Reaction equation

HRID 1646504 reaction equation
[NH2:1][C:2]1[S:3][C:4]([S:7][CH2:8][C:9]2[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[C:11]([OH:18])[C:10]=2[CH2:19][CH2:20][CH3:21])=[N:5][N:6]=1.[C:22]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=1)(=[O:27])[CH2:23][C:24]([O-])=[O:25].C1(N=C=NC2CCCCC2)CCCCC1.C1(C)C=CC(S(O)(=O)=O)=CC=1>N1C=CC=CC=1.C(OCC)(=O)C>[C:15]([C:12]1[CH:13]=[CH:14][C:9]([CH2:8][S:7][C:4]2[S:3][C:2]([NH:1][C:24](=[O:25])[CH2:23][C:22]([O:28][CH2:29][C:30]3[CH:31]=[CH:32][C:33]([O:36][CH3:37])=[CH:34][CH:35]=3)=[O:27])=[N:6][N:5]=2)=[C:10]([CH2:19][CH2:20][CH3:21])[C:11]=1[OH:18])(=[O:17])[CH3:16]

Participants

7

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 10868Dicyclohexylcarbodiimide2×HCID 14053129HCID 14053129, compoundHCID 713318353-[(4-Methoxyphenyl)methoxy]-3-oxopropanoate2×

Product 1

HCID 14053130HCID 14053130, compoundYield 17.4%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 0.14 g of 2-amino-5-[(4-acetyl-3-hydroxy-2-propylbenzyl)thio]-1,3,4-thiadiazole obtained in Example 5 and 0.15 g of mono-p-methoxybenzyl malonate in 3 ml of pyridine were added 0.15 g of dicyclohexylcarbodiimide and a catalytic amount of p-toluenesulfonic acid. The resultant mixture was stirred at room temperature for hours. During the stirring, 0.15 g each of mono-p-methoxybenzyl malonate and dicyclohexylcarbodiimide were supplemented to the system. After completion of the reaction, ethyl acetate was added to the system. After insoluble matters were filtered off, the filtrate was concentrated under reduced pressure The obtained residue was dissolved in chloroform. The solution was washed with, in sequence, 1N hydrochloric acid, water, a saturated aqueous sodium bicarbonate solution and water and then, dried over anhydrous magnesium sulfate The solvent was then removed by distillation. The resultant residue was subjected to silica gel column chromatography followed by elution with a mixture of chloroform-methanol (4:1). The eluate was recrystallized from isopropyl alcohol to give 0.04 g of p-methoxybenzyl 3-[[5-[(4-acetyl-3-hydroxy-2-propylbenzyl)thio]-1,3,4-thiadiazol-2-yl]amino]-3-oxopropionate.

Workup

  1. additionwas added to the system
  2. filtrationAfter insoluble matters were filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure The obtained residue
  4. dissolutionwas dissolved in chloroform
  5. washThe solution was washed with, in sequence, 1N hydrochloric acid, water
  6. dry with materiala saturated aqueous sodium bicarbonate solution and water and then, dried over anhydrous magnesium sulfate The solvent
  7. customwas then removed by distillation
  8. washfollowed by elution with a mixture of chloroform-methanol (4:1)
  9. customThe eluate was recrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-a9a8e952012542f8aa7fc16b03b007d4
Source dataset
uspto-grants-1993_01
Patent number
US05180730

Reaction notes

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