تفاعل #45210

معادلة التفاعل

hexane 2-propanol

hexane

triethylamine

Lansoprazole

→

R(+)-lansoprazole

المردود 27.2%

(R)-2-[[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridinyl]methyl]sulfinyl]-1H-benzimidazole

المردود 27.2%

المذيبات

2-propanol

ظروف التفاعل

المعالجة

1. 1
   أخرىto isolate the individual optical isomers
2. 2
   تركيزconcentrated
3. 3
   workup.DISSOLUTIONdissolved in ethanol (250 ml)
4. 4
   workup.ADDITIONafter triethylamine (3 ml) was added
5. 5
   ترشيحthe solution was filtered through a 0.45 μm
6. 6
   ترشيحfilter
7. 7
   تركيزAfter the filtrate was concentrated
8. 8
   workup.ADDITIONhexane was added
9. 9
   أخرىthe filtrate was again evaporated to dryness

الإجراء التجريبي

Lansoprazole (racemate) (34.2 g) was dissolved in 2-propanol (1,710 ml) and hexane (1,140 ml) containing triethylamine (0.2%) and fractionated by HPLC (column: CHIRALCEL OD 50 mm dia.×500 mm, temperature: room temperature, mobile phase: hexane/2-propanol=85/15, flow rate: 60 ml/min, detection wavelength: 285 nm, 1 shot: about 300 mg) to isolate the individual optical isomers. Fractions of an optical isomer of shorter retention time were combined and concentrated; the individual lots were combined and dissolved in ethanol (250 ml); after triethylamine (3 ml) was added, the solution was filtered through a 0.45 μm filter. After the filtrate was concentrated, hexane was added, and the filtrate was again evaporated to dryness to yield R(+)-lansoprazole (9.31 g, optical purity 98.3% ee) as an amorphous substance.

المصدر