Water → {4-[(E)-2-(4-chloro-2-methoxy-pyridin-3-yl)-vinyl]-3-nitro-phenyl}-carbamic acid tert-butyl ester

HRID 1051214노트

반응식

HRID 1051214 반응식
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH:16](OC(=O)C(F)(F)F)[C:17]2[C:18]([O:24][CH3:25])=[N:19][CH:20]=[CH:21][C:22]=2[Cl:23])=[C:11]([N+:33]([O-:35])=[O:34])[CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O>C1COCC1>[C:1]([O:5][C:6](=[O:7])[NH:8][C:9]1[CH:14]=[CH:13][C:12](/[CH:15]=[CH:16]/[C:17]2[C:18]([O:24][CH3:25])=[N:19][CH:20]=[CH:21][C:22]=2[Cl:23])=[C:11]([N+:33]([O-:35])=[O:34])[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

4

반응물 2

HCID 962WaterHCID 90102788Trifluoro-acetic acid 2-(4-tert-butoxycarbonylamino-2-nitro-phenyl)-1-(4-chloro-2-methoxy-pyridin-3-yl)-ethyl ester

생성물 1

HCID 90102932{4-[(E)-2-(4-chloro-2-methoxy-pyridin-3-yl)-vinyl]-3-nitro-phenyl}-carbamic acid tert-butyl ester수율 68%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
70 °C

실험 절차

A solution of trifluoro-acetic acid 2-(4-tert-butoxycarbonylamino-2-nitro-phenyl)-1-(4-chloro-2-methoxy-pyridin-3-yl)-ethyl ester (crude 1.60 g, 3.08 mmol) in THF (10 mL) was added 8-diazabicyclo[5.4.0]undec-7-ene (1.33 g, 8,74 mmol) at 25° C. The reaction was allowed to stir at 70° C. for 3 hours. The reaction mixture was cooled to 25° C., and poured into water. The aqueous phase was extracted three times with ethyl acetate. The combined organic layers were washed with brine and dried over magnesium sulfate. Filtration followed by concentration in vacuo gave a brown solid. Flash chromatography (80/20 hexanes/ethyl acetate) afforded {4-[(E)-2-(4-chloro-2-methoxy-pyridin-3-yl)-vinyl]-3-nitro-phenyl}-carbamic acid tert-butyl ester (800 mg, 68%) as an oil. MH+ 406.0.

후처리

  1. temperatureThe reaction mixture was cooled to 25° C.
  2. extractionThe aqueous phase was extracted three times with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationFiltration
  6. concentrationfollowed by concentration in vacuo
  7. customgave a brown solid

출처 및 근거

ORD 기록
ord-929b11c3fe034904b4b83a5f1c6dc8b0
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09388166B2

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