Hydrazine hydrate (1:1) → tert-butyl (6-(((2S)-2-acetamidopropyl)oxy)-5-fluoropyridin-3-yl)carbamate

HRID 2277305노트

반응식

HRID 2277305 반응식
[O:1]=[C:2]1[C:10]2C(=CC=CC=2)C(=O)[N:3]1[C@@H:12]([CH3:30])[CH2:13][O:14][C:15]1[N:20]=[CH:19][C:18]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:17][C:16]=1[F:29].O.NN>C1COCC1>[C:2]([NH:3][C@@H:12]([CH3:30])[CH2:13][O:14][C:15]1[N:20]=[CH:19][C:18]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:26])([CH3:25])[CH3:27])=[CH:17][C:16]=1[F:29])(=[O:1])[CH3:10]

참가 물질

4

반응물 2

HCID 24654Hydrazine hydrate (1:1)HCID 86731386tert-butyl (6-(((2S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propyl)oxy)-5-fluoropyridin-3-yl)carbamate

생성물 1

HCID 86731387tert-butyl (6-(((2S)-2-acetamidopropyl)oxy)-5-fluoropyridin-3-yl)carbamate수율 82.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
60 °C

실험 절차

A mixture of tert-butyl (6-(((2S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propyl)oxy)-5-fluoropyridin-3-yl)carbamate (1.62 g), hydrazine monohydrate (0.976 g) and THF (15 mL) was stirred overnight at 60° C. The precipitate was removed by filtration, and the obtained filtrate was concentrated under reduced pressure. The obtained residue was mixed with acetic anhydride (0.736 mL), triethylamine (1.09 mL) and ethyl acetate (15 mL), and the obtained mixture was stirred at 60° C. for 1 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (1.05 g).

후처리

  1. customThe precipitate was removed by filtration
  2. concentrationthe obtained filtrate was concentrated under reduced pressure
  3. additionThe obtained residue was mixed with acetic anhydride (0.736 mL), triethylamine (1.09 mL) and ethyl acetate (15 mL)
  4. stirringthe obtained mixture was stirred at 60° C. for 1 hr
  5. concentrationThe reaction mixture was concentrated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-0762b2c0dbb046fe878589dd5b0b725c
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09133129B2

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