Sodium hydride → N-[4-(E-2-Cyano-2-pyrid-3-ylethenyl)-2-(2-methylphenyl)benzoyl]methionine, Methyl Ester

HRID 2121272노트

반응식

HRID 2121272 반응식
CCOP(O[CH:9]([C:12]1[CH:17]=[CH:16][CH:15]=[N:14][CH:13]=1)[C:10]#[N:11])(CC)=O.[H-].[Na+].[CH3:20][O:21][C:22](=[O:46])[C@H:23]([CH2:42][CH2:43][S:44][CH3:45])[NH:24][C:25](=[O:41])[C:26]1[CH:31]=[CH:30][C:29]([CH:32]=O)=[CH:28][C:27]=1[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[CH3:40]>COCCOC>[C:10](/[C:9](/[C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1)=[CH:32]/[C:29]1[CH:30]=[CH:31][C:26]([C:25]([NH:24][C@H:23]([C:22]([O:21][CH3:20])=[O:46])[CH2:42][CH2:43][S:44][CH3:45])=[O:41])=[C:27]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[CH3:40])[CH:28]=1)#[N:11]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 10596254HCID 10596254, 화합물HCID 88040914Diethyl 3-pyridylcyanomethyl phosphonate

생성물 1

HCID 20622898N-[4-(E-2-Cyano-2-pyrid-3-ylethenyl)-2-(2-methylphenyl)benzoyl]methionine, Methyl Ester

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매

실험 절차

To a solution of diethyl 3-pyridylcyanomethyl phosphonate (269 mg) in DME (3 mL) was added NaH (39 mg@60%). To the red solution was added N-[4-formyl-2-(2-methylphenyl)benzoyl] methionine methyl ester (example 10756, 340 mg). After 30 min, the reaction was warmed to reflux for 2.5 h. The reaction was cooled, quenched with water (5 mL), and extracted into EtOAc (20 mL). The organic extracts were washed with brine (5 mL), dried (MgSO4), filtered and concentrated. The residue was purified by silica gel chromatography eluting with 50%-100% EtOAc/hexane to afford two products as colorless oils. The more mobile isomer (68 mg, 13%) was assigned the Z configuration based on a ROESY experiment. MS (APCI(+)) m/e 486 (M+H)+. MS (APCI(−)) m/e 485 M−. The less mobile isomer (246 mg, 48%) was assigned the E configuration based on a ROESY experiment. MS (APCI(+)) m/e 486 (M+H)+. MS (APCI(−)) m/e 485 M−.

후처리

  1. temperaturethe reaction was warmed
  2. temperatureto reflux for 2.5 h
  3. temperatureThe reaction was cooled
  4. customquenched with water (5 mL)
  5. extractionextracted into EtOAc (20 mL)
  6. washThe organic extracts were washed with brine (5 mL)
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was purified by silica gel chromatography
  11. washeluting with 50%-100% EtOAc/hexane
  12. customto afford two products as colorless oils

출처 및 근거

ORD 기록
ord-167a51ac699c47d6a3cc6d903a5fc671
출처 데이터셋
uspto-grants-2004_02
특허 번호
US06693123B2

반응 노트

불러오는 중…