Reacción #218745

Ecuación de reacción

sodium bicarbonate

tetrabutylammonium fluoride

product

6-[(4,5-Dichloro-2-oxo-3(2H)-thiazolyl)methyl]-5-[4-[(1,1-dimethylethyl)dimethylsilyloxy]isoxazolidin-2-ylcarbonyl]-3-methyl-1-(isobutyl)-thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

acetic acid

→

title compound

6-[(4,5-Dichloro-2-oxo-3(2H)-thiazolyl)methyl]-5-[4-hydroxyisoxazolidin-2-ylcarbonyl]-3-methyl-1-(isobutyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

Disolventes

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónextracted into ethyl acetate
2. 2
   LavadoThe organics were washed with water
3. 3
   Secadodried over magnesium sulphate
4. 4
   ConcentraciónConcentration in vacuo
5. 5
   Otrogave a white solid
6. 6
   Otrothat was purified by reverse phase HPLC

Procedimiento

To a solution of the product of step e) (180 mg) in THF (5 ml) under a nitrogen atmosphere, was added glacial acetic acid (0.10 ml) follwed by 1 N tetrabutylammonium fluoride solution in THF (0.5 ml). After 16 h at ambient temperature the mixture was neutralised with sat sodium bicarbonate solution and extracted into ethyl acetate. The organics were washed with water, and dried over magnesium sulphate. Concentration in vacuo gave a white solid that was purified by reverse phase HPLC to give the title compound as a white solid (100 mg). δ 1HDMSO 0.92 (6H,d), 2.18 (1H,non), 3.20 (3H,s), 3.43-4.11 (6H,m), 4.60-4.76 (1H,m), 5.04-5.11 (2H,m), 5.51 (1H,s).

Fuente