Water → (2S,4R)-1-t-butoxycarbonyl-2-[(Z)-5-carboxy-1-pentenyl]-4-(4-chlorophenylsulfonylamino)pyrrolidine

To a suspension of (4-carboxybutyl)triphenylphosphonium bromide (13.3 g) in a mixture of tetrahydrofuran (80 ml) and hexamethylphosphoramide (20 ml) was added a solution (60 ml, 1M solution) of lithium bis(trimethylsilyl)amide in tetrahydrofuran at 0° C. and the solution was stirred at room temperature for 1 hour. After the solution was cooled to -25° C., a solution of (2S,4R)-1-t-butoxycarbonyl-4-(4-chlorophenylsulfonylamino)-2-formylpyrrolidine (3.89 g) in tetrahydrofuran (20 ml) was added dropwise thereto and the solution was stirred at -20° C.~-25° C. for 30 minutes. Water (100 ml) and ethyl acetate (100 ml) were added to the solution and the aqueous phase was separated. The aqueous solution was adjusted to pH2 with 1N hydrochloric acid and extracted with ethyl acetate (200 ml). The organic layer was washed two times with water and then with brine and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was chromatographed on a silica gel (150 g) column with a mixture of chloroform and methanol (30:1) as an eluent to give (2S,4R)-1-t-butoxycarbonyl-2-[(Z)-5-carboxy-1-pentenyl]-4-(4-chlorophenylsulfonylamino)pyrrolidine (2.98 g) as a colorless oil.

1. temperatureAfter the solution was cooled to -25° C.
2. stirringthe solution was stirred at -20° C.~-25° C. for 30 minutes
3. customthe aqueous phase was separated
4. extractionextracted with ethyl acetate (200 ml)
5. washThe organic layer was washed two times with water
6. dry with materialwith brine and dried over magnesium sulfate
7. customThe solvent was evaporated in vacuo
8. customthe residue was chromatographed on a silica gel (150 g) column with a mixture of chloroform and methanol (30:1) as an eluent

ORD-Eintrag

ord-f43d5eb010c44566a40f51c1565ebb1a

Quelldatensatz

uspto-grants-1993_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05264453