تفاعل #6862

معادلة التفاعل

product

1-(2-Ethoxy-2-oxoethyl)-2-(1-(S)-(((Phenylmethoxy)carbonyl)-amino)-pentyl)-4-(2-methoxyphenyl)-imidazole

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product

المردود 87.0%

8-Butyl-6-oxo-2-(2-methoxyphenyl)-imidazo[1,2-a]pyrazine

المردود 87.0%

المذيبات

HOAc

ظروف التفاعل

المعالجة

1. 1
   أخرىThe catalyst was removed by filtration through a 3 cm pad of diatomaceous earth
2. 2
   تركيزThe mixture was concentrated to a solid under reduced pressure
3. 3
   workup.DISSOLUTIONdissolved in CH2Cl2 (100 ml)
4. 4
   غسيلwashed with saturated NaHCO3 solution (125 ml)
5. 5
   تجفيفThe CH2Cl2 layer was dried over Na2SO4
6. 6
   ترشيحfiltered
7. 7
   workup.ADDITION275 ml hexanes was added
8. 8
   ترشيحProduct was filtered off
9. 9
   أخرىdried to constant weight

الإجراء التجريبي

The product from Step 1.d. (compound v where R3 is n-butyl, R4 is 2-methoxyphenyl, and R5 and R6 are H) (11.5 g, 23.9 mmol) was dissolved in HOAc (100 ml) containing 10% Pd on carbon catalyst (500 mg) and hydrogenated under 50 psi of H2 for about 3 hours at room temperature. The catalyst was removed by filtration through a 3 cm pad of diatomaceous earth and the filtrate was warmed at about 70° C. for about 2 hours. The mixture was concentrated to a solid under reduced pressure, dissolved in CH2Cl2 (100 ml) and washed with saturated NaHCO3 solution (125 ml). The CH2Cl2 layer was dried over Na2SO4, filtered and 275 ml hexanes was added. Product was filtered off and dried to constant weight to yield 6.21 g (87%) of product, m.r.=200–202° C., NMR (300 MHz, DMSO-d6, 30° C.) 8.5–8.6 (1H s), 8.0–8.1 (1H, d), 7.4–7.6 (1H, s), 7.1–7.3 (1H, t), 7.0–7.1 (1H, d), 6.9–7.1 (1H, t), 4.55–4.8 (2H, q), 4.55–4.7 (1H, t), 3.8–4.0 (3H, s), 1.75–1.95 (2H, m), 1.1–1.5 (4H, m), 0.8–0.9 (3H, t).

المصدر