Sodium → Methyl (3S,E)-5-[4,5-bis(4-fluorophenyl)-2-(1-methylethyl)-1H-imidazol-1-yl]-3-hydroxy-4-pentenoate

A stirred suspension of (S)-1-hydroxy-1,1,2-triphenyleth-2-yl(3S,E)-5-[4,5-bis(4-fluorophenyl)-2-(1-methylethyl)-1H-imidazol-1-yl]-3-hydroxy-4-pentenoate (3.11 g) in methanol (30 ml) was treated with a solution of sodium (110 mg) in methanol (20 ml) plus methanol washings (2×5 ml). The resulting orange solution was stirred at room temperature for 2.5 h then the reaction mixture was concentrated. This was dissolved in dichloromethane (150 ml) and the solution was washed with water (50 ml) and brine (2×50 ml). The combined washings were extracted with dichloromethane (50 ml) and the combined organic phases were dried and evaporated to a pale buff solid (3.13 g). This was purified by CC eluting with System A 1:1 to give the title compound (1.588 g) as a white crystalline solid, νmax (nujol) 1738 cm-1 (C=O).

1. concentrationthe reaction mixture was concentrated
2. dissolutionThis was dissolved in dichloromethane (150 ml)
3. washthe solution was washed with water (50 ml) and brine (2×50 ml)
4. extractionThe combined washings were extracted with dichloromethane (50 ml)
5. customthe combined organic phases were dried
6. customevaporated to a pale buff solid (3.13 g)
7. customThis was purified by CC
8. washeluting with System A 1:1

ORD-Eintrag

ord-4bdb3f98d28847aa861f055f03b706d8

Quelldatensatz

uspto-grants-1991_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05013749