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Potassium Carbonate → 2-(4-Bromo-2-fluorobenzyl)-4-(-)-menthyloxycarbonyl-1,3-dioxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-4-acetic acid tert-butyl ester

HRID 256592
ノート
印刷プレビュー

反応式

HRID 256592 の反応式
[CH:1]1([CH3:33])[CH2:6][CH2:5][CH:4]([CH:7]([CH3:9])[CH3:8])[CH:3]([O:10][C:11]([CH:13]2[N:18]3[CH:19]=[CH:20][CH:21]=[C:17]3[C:16](=[O:22])[N:15]([CH2:23][C:24]3[CH:29]=[CH:28][C:27]([Br:30])=[CH:26][C:25]=3[F:31])[C:14]2=[O:32])=[O:12])[CH2:2]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:41][C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43]>CN(C)C=O>[C:45]([O:44][C:42](=[O:43])[CH2:41][C:13]1([C:11]([O:10][CH:3]2[CH:4]([CH:7]([CH3:8])[CH3:9])[CH2:5][CH2:6][CH:1]([CH3:33])[CH2:2]2)=[O:12])[N:18]2[CH:19]=[CH:20][CH:21]=[C:17]2[C:16](=[O:22])[N:15]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([Br:30])=[CH:26][C:25]=2[F:31])[C:14]1=[O:32])([CH3:48])([CH3:47])[CH3:46]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 867473472-(4-Bromo-2-fluorobenzyl)-1,3-dioxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-4-carboxylic acid (-)-menthyl ester

生成物 1

HCID 677225582-(4-Bromo-2-fluorobenzyl)-4-(-)-menthyloxycarbonyl-1,3-dioxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-4-acetic acid tert-butyl ester

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

反応条件

温度
70 °C

実験手順

A mixture of 2-(4-bromo-2-fluorobenzyl)-1,3-dioxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-4-carboxylic acid (-)-menthyl ester (67.0 g), anhydrous potassium carbonate (36.0 g) and tert-butyl bromoacetate (33.0 g) in anhydrous dimethylformamide (200 ml) was stirred under the stream of nitrogen at 70° C. for 2.5 hours. After removal of the insoluble materials by filtration, the filtrate was poured into water and extracted with ethyl acetate. The extracts were washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and evaporated under reduced pressure. The residue was recrystallized from n-hexane to give the title compound (Diastereomer A) (23.5 g, 28.8%) as colorless crystals, mp 99°-100° C.

後処理

  1. customAfter removal of the insoluble materials
  2. filtrationby filtration
  3. additionthe filtrate was poured into water
  4. extractionextracted with ethyl acetate
  5. washThe extracts were washed with saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated under reduced pressure
  8. customThe residue was recrystallized from n-hexane

出典と根拠

ORDレコード
ord-7ea79379214647d1805da693ef93ec4c
出典データセット
uspto-grants-1993_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05258382

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート