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HCID 59556982、化合物 → HCID 58238347、化合物

HRID 1173603
ノート
印刷プレビュー

反応式

HRID 1173603 の反応式
C(OC([NH:11][C@@H:12]([CH3:32])[CH:13]([C:22]1([C:25](OC(C)(C)C)=[O:26])[CH2:24][CH2:23]1)[O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])=O)C1C=CC=CC=1>CO.[C].[Pd]>[Si:15]([O:14][CH:13]1[C:22]2([CH2:24][CH2:23]2)[C:25](=[O:26])[NH:11][C@H:12]1[CH3:32])([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 1

HCID 59556982HCID 59556982、化合物

生成物 1

HCID 58238347HCID 58238347、化合物収率 60%

試薬・触媒・溶媒 2

HCID 178418390HCID 178418390、化合物触媒HCID 887Methanol溶媒

実験手順

To a solution of tert-butyl 1-((2S)-2-{[(benzyloxy)carbonyl]amino}-1-(tert-butyldimethylsilyloxy)propyl)cyclopropanecarboxylate (693.9 mg) in methanol (8 mL) was added 10% palladium carbon (containing 50% water, 80 mg), and the mixture was stirred at room temperature for 3 hr under a hydrogen atmosphere and filtered. The filtrate was concentrated under reduced pressure, and the residue was dissolved in methanol (10 mL). Sodium methoxide (404 mg) was added and the mixture was refluxed for 4 hr. A saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=30/1→1/3) to give the title compound as a colorless solid (yield: 200.8 mg, yield: 60%).

後処理

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in methanol (10 mL)
  4. additionSodium methoxide (404 mg) was added
  5. temperaturethe mixture was refluxed for 4 hr
  6. additionA saturated aqueous ammonium chloride solution was added to the reaction mixture
  7. extractionthe mixture was extracted with ethyl acetate
  8. washThe extract was washed with saturated brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=30/1→1/3)

出典と根拠

ORDレコード
ord-d6db27740f614bb79b219724af4f77cb
出典データセット
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07834051B2

反応ノート

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