Trifluoroacetic acid → Ethyl 6-(4-fluorobenzyl)-4-hydroxy-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxylate

HRID 1817301노트

반응식

HRID 1817301 반응식
C(O[C:6]1[O:10][C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[N:8][CH:7]=1)CCC.[F:16][C:17]1[CH:30]=[CH:29][C:20]([CH2:21][N:22]2[CH2:27][CH2:26][CH:25]=[CH:24][C:23]2=[O:28])=[CH:19][CH:18]=1.FC(F)(F)C(O)=O>CCOCC>[F:16][C:17]1[CH:18]=[CH:19][C:20]([CH2:21][N:22]2[CH2:27][CH2:26][C:25]3[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[N:8][CH:7]=[C:6]([OH:10])[C:24]=3[C:23]2=[O:28])=[CH:29][CH:30]=1

참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 66996945Ethyl 5-butoxy-1,3-oxazole-2-carboxylateHCID 690647451-(4-Fluorobenzyl)-5,6-dihydropyridin-2-(1H)-one

생성물 1

HCID 69061030Ethyl 6-(4-fluorobenzyl)-4-hydroxy-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxylate

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

반응 조건

온도
130 °C

실험 절차

In a heavy walled round bottom flask with screw top were combined ethyl 5-butoxy-1,3-oxazole-2-carboxylate (2.53 g, 11.88 mmol) and 1-(4-fluorobenzyl)-5,6-dihydropyridin-2-(1H)-one (1.22 g, 5.94 mmol; see Example 1, Step 3) and trifluoroacetic acid (0.46 mL, 5.94 mmol). The vessel was sealed and placed in an oil bath heated to 130° C. The reaction mixture was stirred for 3 days. The dark brown reaction mixture was cooled and a crystalline precipitate formed. The mixture was diluted with ether and the solids collected by filtration and washed with ether to give the product as tan shiny plates. Further product can be obtained by evaporating the mother liquor, adding more trifluoroacetic acid and re-heating the mixture.

후처리

  1. customIn a heavy walled round bottom flask with screw top were combined
  2. customThe vessel was sealed
  3. customplaced in an oil bath
  4. temperatureThe dark brown reaction mixture was cooled
  5. customa crystalline precipitate formed
  6. filtrationthe solids collected by filtration
  7. washwashed with ether
  8. customto give the product as tan shiny plates
  9. customFurther product can be obtained
  10. customby evaporating the mother liquor
  11. additionadding more trifluoroacetic acid
  12. temperaturere-heating the mixture

출처 및 근거

ORD 기록
ord-0ce00a3796854952bb87784b3e95aed3
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07598264B2

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