Acetic Acid → N-(1-Adamantylmethyl)-5-chloro-2-formylisonicotinamide

HRID 1247607노트

반응식

HRID 1247607 반응식
[C:1]12([CH2:11][NH:12][C:13](=[O:23])[C:14]3[C:19]([Cl:20])=[CH:18][N:17]=[C:16]([CH:21]=C)[CH:15]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C(O)(=[O:26])C>ClCCl>[C:1]12([CH2:11][NH:12][C:13](=[O:23])[C:14]3[C:19]([Cl:20])=[CH:18][N:17]=[C:16]([CH:21]=[O:26])[CH:15]=3)[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH2:2]1)[CH2:10]2

참가 물질

4

반응물 2

HCID 176Acetic AcidHCID 21906707N-(1-Adamantylmethyl)-5-chloro-2-vinylisonicotinamide

생성물 1

HCID 21906741N-(1-Adamantylmethyl)-5-chloro-2-formylisonicotinamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
-78 °C

실험 절차

N-(1-Adamantylmethyl)-5-chloro-2-vinylisonicotinamide (Example 29(i)) (1.70 g) was dissolved in dichloromethane (50 mL), treated with acetic acid (1 mL) and cooled to −78° C. under nitrogen. Ozone was bubbled through the resulting solution for 2 hours while maintaining the temperature. Nitrogen was subsequently bubbled through the solution for 10 minutes and dimethylsulfide (2 mL) was added. The solution was warmed to room temperature washed with sodium bicarbonate (2×10 mL) and brine (30 mL); the organics were dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by chromatography on silica gel eluting with ethyl acetate:dichloromethane (1:20) to afford the sub-titled compound (1.13 g).

후처리

  1. customOzone was bubbled through the resulting solution for 2 hours
  2. temperaturewhile maintaining the temperature
  3. customNitrogen was subsequently bubbled through the solution for 10 minutes
  4. additiondimethylsulfide (2 mL) was added
  5. temperatureThe solution was warmed to room temperature
  6. washwashed with sodium bicarbonate (2×10 mL) and brine (30 mL)
  7. dry with materialthe organics were dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was purified by chromatography on silica gel eluting with ethyl acetate:dichloromethane (1:20)

출처 및 근거

ORD 기록
ord-01fbfe563b2c4ee481ced2672ef9c963
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07129246B2

반응 노트

불러오는 중…