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1-Pentanol → N-[(R)-1-[3-(1-tert-butoxycarbonyl-4-piperidyl)-(E)-acryloyl]-3-piperidylcarbonyl]-3(S)-ethynyl-beta-alanine n-pentyl ester

HRID 1934395
ノート
印刷プレビュー

反応式

HRID 1934395 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11](/[CH:14]=[CH:15]/[C:16]([N:18]2[CH2:23][CH2:22][CH2:21][C@@H:20]([C:24]([NH:26][C@H:27]([C:32]#[CH:33])[CH2:28][C:29]([OH:31])=[O:30])=[O:25])[CH2:19]2)=[O:17])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:34](O)[CH2:35][CH2:36][CH2:37][CH3:38].Cl.C(N=C=NCCCN(C)C)C>ClCCl>[CH2:34]([O:30][C:29](=[O:31])[CH2:28][C@@H:27]([C:32]#[CH:33])[NH:26][C:24]([C@@H:20]1[CH2:21][CH2:22][CH2:23][N:18]([C:16](=[O:17])/[CH:15]=[CH:14]/[CH:11]2[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:7])[CH2:13][CH2:12]2)[CH2:19]1)=[O:25])[CH2:35][CH2:36][CH2:37][CH3:38]
参加物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 62761-PentanolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86758027N-[(R)-1-[3-(1-tert-butoxycarbonyl-4-piperidyl)-(E)-acryloyl]-3-piperidylcarbonyl]-3(S)-ethynyl-beta-alanine

生成物 1

HCID 86758033N-[(R)-1-[3-(1-tert-butoxycarbonyl-4-piperidyl)-(E)-acryloyl]-3-piperidylcarbonyl]-3(S)-ethynyl-beta-alanine n-pentyl ester収率 94%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a mixture of N-[(R)-1-[3-(1-tert-butoxycarbonyl-4-piperidyl)-(E)-acryloyl]-3-piperidylcarbonyl]-3(S)-ethynyl-β-alanine (0.6 g), n-pentylalcohol (0.16 ml) and N,N-dimethylaminopyridine (16 mg) in dichloromethane (6 ml) was added 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (0.27 g) at 0° C. After stirring at room temperature for overnight, the solution was evaporated in vacuo. The residue was poured into water and extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogencarbonate, water and brine, dried over MgSO4, and evaporated in vacuo, subsequently. The residue was purified by column chromatography on silica gel eluting with AcOEt:Hexane=(1:1) to give N-[(R)-1-[3-(1-tert-butoxycarbonyl-4-piperidyl)-(E)-acryloyl]-3-piperidylcarbonyl]-3(S)-ethynyl-β-alanine n-pentyl ester as a colorless oil (0.65 g, 94.0%).

後処理

  1. customthe solution was evaporated in vacuo
  2. additionThe residue was poured into water
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with saturated aqueous sodium hydrogencarbonate, water and brine
  5. dry with materialdried over MgSO4
  6. customevaporated in vacuo
  7. customThe residue was purified by column chromatography on silica gel eluting with AcOEt

出典と根拠

ORDレコード
ord-519d8538e9b641798729c15d232759f1
出典データセット
uspto-grants-2002_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06384028B1

反応ノート

読み込み中…

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