تفاعل #46288

معادلة التفاعل

hydrochloric acid

ethyl 3-(acetyloxy)-6-(3-chloro-4-fluorobenzyl)-4-methoxy-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxylate

lithium hydroxide monohydrate

water

→

title acid

6-(3-Chloro-4-fluorobenzyl)-4-methoxy-3,5-dioxo-2,3,5,6,7,8-hexahydro-2,6-naphthyridine-1-carboxylic acid

المذيبات

ethanol

ظروف التفاعل

المعالجة

1. 1
   أخرىwas sonicated for 20 minutes
2. 2
   درجة الحرارةThe reaction mixture was cooled in an ice-water bath
3. 3
   ترشيحThe resultant light yellow solid was filtered
4. 4
   غسيلwashed successively with water (1 L)
5. 5
   workup.ADDITIONa 3:2 v/v mixture of water and ethanol (500 mL), MTBE (750 mL), and air
6. 6
   أخرىdried
7. 7
   workup.DISSOLUTIONThe yellow solid was dissolved in anhydrous DMF (700 mL)
8. 8
   تركيزconcentrated under vacuum
9. 9
   أخرىto remove residual water
10. 10
    أخرىThe yellow solid was triturated with MTBE
11. 11
    ترشيحfiltered
12. 12
    أخرىstored under vacuum overnight

الإجراء التجريبي

A mixture of ethyl 3-(acetyloxy)-6-(3-chloro-4-fluorobenzyl)-4-methoxy-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxylate (217 g, 0.48 mol), lithium hydroxide monohydrate (70.7 g, 1.67 mol), and water (320 mL) in ethanol (1.8 L) was sonicated for 20 minutes. The reaction mixture was cooled in an ice-water bath and treated with hydrochloric acid (425 mL, 3 M). The resultant light yellow solid was filtered, washed successively with water (1 L), a 3:2 v/v mixture of water and ethanol (500 mL), MTBE (750 mL), and air dried. The yellow solid was dissolved in anhydrous DMF (700 mL) and concentrated under vacuum. The procedure was repeated twice to remove residual water. The yellow solid was triturated with MTBE, filtered, and stored under vacuum overnight to afford the title acid.

المصدر