تفاعل #218745

معادلة التفاعل

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

المذيبات

THF

THF

ظروف التفاعل

المعالجة

1. 1
   استخلاصextracted into ethyl acetate
2. 2
   غسيلThe organics were washed with water
3. 3
   تجفيفdried over magnesium sulphate
4. 4
   تركيزConcentration in vacuo
5. 5
   أخرىgave a white solid
6. 6
   أخرىthat was purified by reverse phase HPLC

الإجراء التجريبي

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).

المصدر