تفاعل #64437

معادلة التفاعل

amide

N-tosyl-4-oxo-1,2,3,4-tetrahydroisoquinoline

ethenylidenebisphosphonic acid tetraethyl ester

DBU

THF

→

title compound

[3-(2-Pyridinylamino-carbonyl)-4-oxo-4-phenyl-butylidene]bisphosphonic acid tetraethyl ester

المذيبات

ether

ethyl acetate

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe reaction is cooled
2. 2
   استخلاصextracted with hydrochloric acid (10%, 3×)
3. 3
   غسيلAfter back washing with ethyl acetate
4. 4
   استخلاصextracted with methylene chloride
5. 5
   تجفيفdried with magnesium sulfate
6. 6
   تركيزconcentrated under reduced pressure
7. 7
   أخرىThe crude material is chromatographed
8. 8
   غسيلeluting with ethyl acetate and acetone
9. 9
   تركيزThe resulting oil is concentrated under reduced pressure from ether
10. 10
    أخرىto give a solid
11. 11
    ترشيحfiltered
12. 12
    أخرىdried under reduced pressure

الإجراء التجريبي

The amide (II, 2.52 g), ethenylidenebisphosphonic acid tetraethyl ester (I, 3.00 g), and DBU (0.25 ml) are heated to 50° C. in THF (20 ml) for 3 hrs. The reaction is cooled, diluted with ethyl acetate, then extracted with hydrochloric acid (10%, 3×). After back washing with ethyl acetate, the acidic fraction is neutralized with saturated sodium bicarbonate, extracted with methylene chloride, dried with magnesium sulfate, and concentrated under reduced pressure. The crude material is chromatographed eluting with ethyl acetate and acetone. The resulting oil is concentrated under reduced pressure from ether to give a solid. The solid is slurried in ether, filtered and dried under reduced pressure to give the title compound, mp 104°-105°; MS (m/e) 540, 435, 420, 403, 163, 121, 105 and 94; IR (mineral oil) 1705, 1679, 1596, 1578, 1543, 1435 and 1256 cm-1 ; NMR (CDCl3) 9.77, 8.28, 8.10, 7.60, 7.47, 7.01, 5.16, 4.16, 2.65, 1.34 and 1.26 δ; CMR (CDCl3) 202.9, 195.5, 167.6, 151.1, 147.6, 138.4, 136.0, 133.7, 128.9, 128.7, 119.9, 114.1, 63.0 (m), 54.1, 34.5, 25.9 and 16.3 δ.

المصدر