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ChemicalBook CAS DataBase List 3,5-Di(tert-butyldimethylsilyl) Rosuvastatin

3,5-Di(tert-butyldimethylsilyl) Rosuvastatin synthesis

2synthesis methods
6-Heptenoic acid, 3,5-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-7-[4-(4-fluorophenyl)-6-(1-methylethyl)-2-[methyl(methylsulfonyl)amino]-5-pyrimidinyl]-, methyl ester, (3R,5S,6E)-

1353050-09-5
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Yield:1353050-10-8 53%

Reaction Conditions:

with lithium hydroxide in methanol at 20; for 12 h;

Steps:

17.AV

AV) (3R, 5S,E) -3, 5-bis (tert-butyldimethylsilyloxy) -7- (4- (4- fluorophenyl ) -6-isopropyl-2- (N-methylmethylsulfonamido) pyrimidin-5-yl ) hept- 6-enoic acidTo a solution of compound AU) (0.4 g, 0.55 mmol) in THF (3 mL) and MeOH (2 mL) , LiOH (0.04 g, 1.65 mmol) was added. The reaction was stirred at room temperature for 12 hours. The solution was diluted with AcOEt (50 mL) and washed with ?0 (4x30 mL) and brine, then dried over Na2S04 and concentrated under reduced pressure. The residue was purified by flash chromatography (Biotage System, SNAP Cartridge silica 50 g, gradient from n-hexane/AcOEt 8/2 to n-hexane/AcOEt 7/3 during 900 mL) affording the title compound (0.21 g, yield 53%).

References:

WO2011/160974,2011,A2 Location in patent:Page/Page column 60-61