Reacción #343795

Ecuación de reacción

[[5-[[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propyl]thio]-1,3,4-thiadiazol-2-yl]thio]acetic acid

dicyclohexylcarbodiimide

1-hydroxybenzotriazole

N-methylhydroxylamine.hydrochloride

→

2-[[5-[[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propyl]thio]-1,3,4-thiadiazol-2-yl]thio]-N-hydroxy-N-methylacetamide

Rendimiento 36.8%

Disolventes

ethyl acetate

tetrahydrofuran

ethyl acetate

N,N-dimethylformamide

triethylamine

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added
2. 2
   FiltraciónThen, insoluble matters were filtered off
3. 3
   Otrothe filtrate thus formed
4. 4
   Concentraciónwas concentrated under reduced pressure
5. 5
   OtroTo the residue thus formed
6. 6
   Lavadothe mixture was washed with water
7. 7
   Lavadowashed with a diluted aqueous solution of sodium hydrogencarbonate, and water
8. 8
   Secadodried over anhydrous magnesium sulfate
9. 9
   Concentraciónconcentrated under reduced pressure
10. 10
    OtroTo the residue thus obtained
11. 11
    Filtracióninsoluble materials were filtered off
12. 12
    Otrothe filtrate formed
13. 13
    Concentraciónwas concentrated
14. 14
    OtroThe residue thus obtained
15. 15
    Otrowas recrystallized from a mixture of toluene and n-hexane

Procedimiento

To a mixture of 0.5 g of [[5-[[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propyl]thio]-1,3,4-thiadiazol-2-yl]thio]acetic acid obtained in example 22, 0.23 g of dicyclohexylcarbodiimide, 0.14 g of 1-hydroxybenzotriazole, and 50 ml of tetrahydrofuran was added a mixture of 0.27 g of N-methylhydroxylamine.hydrochloride, 0.3 g of triethylamine, and 5 ml of N,N-dimethylformamide and the resultant mixture was stirred overnight at room temperature. Then, insoluble matters were filtered off and the filtrate thus formed was concentrated under reduced pressure. To the residue thus formed was added 100 ml of ethyl acetate and the mixture was washed with water, washed with a diluted aqueous solution of sodium hydrogencarbonate, and water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. To the residue thus obtained was added ethyl acetate, then insoluble materials were filtered off and the filtrate formed was concentrated. The residue thus obtained was recrystallized from a mixture of toluene and n-hexane to provide 0.18 g of 2-[[5-[[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propyl]thio]-1,3,4-thiadiazol-2-yl]thio]-N-hydroxy-N-methylacetamide.

Fuente