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

HRID 2277305ノート

反応式

HRID 2277305 の反応式
[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]

参加物

4

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-0762b2c0dbb046fe878589dd5b0b725c
出典データセット
uspto-grants-2015_09
特許番号
US09133129B2

反応ノート

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