ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

Formic Acid → 2-[4-(tert-Butoxycarbonyl)benzyl]-4-[1-(2-ethoxy-2-oxoethyl)cyclopropyl]butanoic acid

HRID 1920590
ノート
印刷プレビュー

反応式

HRID 1920590 の反応式
C(N(CC)CC)C.C(O)=O.[C:11]([O:15][C:16]([C:18]1[CH:48]=[CH:47][C:21]([CH2:22][C:23]([CH2:36][CH2:37][C:38]2([CH2:41][C:42]([O:44][CH2:45][CH3:46])=[O:43])[CH2:40][CH2:39]2)(C(OCC=C)=O)[C:24]([O:26]CC=C)=[O:25])=[CH:20][CH:19]=1)=[O:17])([CH3:14])([CH3:13])[CH3:12].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:11]([O:15][C:16]([C:18]1[CH:48]=[CH:47][C:21]([CH2:22][CH:23]([CH2:36][CH2:37][C:38]2([CH2:41][C:42]([O:44][CH2:45][CH3:46])=[O:43])[CH2:40][CH2:39]2)[C:24]([OH:26])=[O:25])=[CH:20][CH:19]=1)=[O:17])([CH3:13])([CH3:12])[CH3:14]
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

7

反応物 4

HCID 284Formic AcidHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 57965749Diallyl [4-(tert-butoxycarbonyl)benzyl]{2-[1-(2-ethoxy-2-oxoethyl)cyclopropyl]ethyl}malonate

生成物 1

HCID 579657452-[4-(tert-Butoxycarbonyl)benzyl]-4-[1-(2-ethoxy-2-oxoethyl)cyclopropyl]butanoic acid

試薬・触媒・溶媒 2

HCID 167845
palladium(II) acetate
触媒
HCID 312751,4-Dioxane溶媒2 回

反応条件

温度
100 °C

実験手順

At room temperature, a solution of 7.42 ml (53.56 mmol) of triethylamine and 1.53 ml (40 mmol) of formic acid in 25 ml of dioxane is added to a solution of 8.58 g (16.2 mmol) of diallyl [4-(tert-butoxycarbonyl)benzyl]{2-[1-(2-ethoxy-2-oxoethyl)cyclopropyl]ethyl}malonate, 298 mg (1.14 mmol) of triphenylphosphine and 73 mg (0.33 mmol) of palladium acetate in 75 ml of dioxane. The reaction mixture is then stirred at 100° C. for 2 hours. After complete conversion, the reaction solution is cooled and the solvent is removed under reduced pressure. The residue is then taken up in ethyl acetate and water and acidified with 1 N hydrochloric acid (pH 4-5), and the organic phase is separated off. The aqueous phase is extracted three more times with ethyl acetate, and the organic phases are then combined, washed with saturated sodium chloride solution and dried over sodium sulfate. After filtration, the solution is concentrated under reduced pressure. The crude product obtained is purified by flash chromatography on silica gel (700 g; mobile phase: petroleum ether/ethyl acetate 1:1). This gives 4.9 g (74.6% of theory) of a colorless solid.

後処理

  1. temperatureAfter complete conversion, the reaction solution is cooled
  2. customthe solvent is removed under reduced pressure
  3. customthe organic phase is separated off
  4. extractionThe aqueous phase is extracted three more times with ethyl acetate
  5. washwashed with saturated sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. filtrationAfter filtration
  8. concentrationthe solution is concentrated under reduced pressure

出典と根拠

ORDレコード
ord-d81ed0b128474404a0baf6cf7893e6c4
出典データセット
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08168821B2

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