HCID 54456902, compound → HCID 53743378, compound

(1 -2)A 2.04 g of benzyl (2R,3R)-3-cyclopropyl-2,3-epoxypropionate is dissolved in 40 ml of tetrahydrofuran and subjected to catalytic hydrogenation at room temperature under atmospheric pressure using 1 g of 10% palladium-carbon. After 2 hours, the catalyst is removed by filtration. After 40 ml of toluene is added to the filtrate, the resulting mixture is concentrated under reduced pressure to remove tetrahydrofuran to give a solution of (2R,3R)-3-cyclopropyl-2,3-epoxypropionic acid in toluene. Then, 2.74 g of 4α-acetoxy-2α-benzoyloxy-5β,20-epoxy-1β,13α-dihydroxy-7β,10 β-bis(2,2,2-trichloroethoxycarbonyloxy)tax-11-en-9-one, 1.89 g of 1,3-dicyclohexylcarbodiimide and 187 mg of 4-dimethylaminopyridine are added to the resulting solution of (2R,3R)-3-cyclopropyl-2,3-epoxypropionic acid in toluene. The mixture is stirred at 80° C. for one hour. The reaction mixture is cooled to room temperature and treated in the same manner as described in Example 4(1-1). The residue is purified by silica gel frash column chromatography (solvent; ethyl acetate:hexane=1:2) to give 3.02 g of 4α-acetoxy-2 α-benzoyloxy-13α-[(2R,3R)-3-cyclopropyl-2,3-epoxypropionyloxy]-5β,20-epoxy-1 β-hydroxy-7β,10β-bis(2,2,2-trichloroethoxycarbonyloxy)tax-11-en-9-one. The physical properties of the product are the same as those of the compound of Example 4(1-1).

1. customsubjected to catalytic hydrogenation at room temperature under atmospheric pressure
2. customthe catalyst is removed by filtration
3. additionAfter 40 ml of toluene is added to the filtrate
4. concentrationthe resulting mixture is concentrated under reduced pressure
5. customto remove tetrahydrofuran

ORD record

ord-0ed7709b68484174b5a0523a6b772dce

Source dataset

uspto-grants-1996_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05589502