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N-((1,1-dimethylethoxy)carbonyl)-beta-alanine → (S)-3-tert-Butoxycarbonylamino-1-[4-({[2-(2,3-dihydrobenzofuran-5-yl)-1-methylethyl]ethylamino}methyl)piperidin-1-yl]-propan-1-one

HRID 429831
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 429831
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C:11]([OH:13])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[O:14]1[C:18]2[CH:19]=[CH:20][C:21]([CH2:23][C@@H:24]([N:26]([CH2:29][CH:30]3[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]3)[CH2:27][CH3:28])[CH3:25])=[CH:22][C:17]=2[CH2:16][CH2:15]1>ClCCl>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C:11]([N:33]1[CH2:34][CH2:35][CH:30]([CH2:29][N:26]([C@@H:24]([CH3:25])[CH2:23][C:21]2[CH:20]=[CH:19][C:18]3[O:14][CH2:15][CH2:16][C:17]=3[CH:22]=2)[CH2:27][CH3:28])[CH2:31][CH2:32]1)=[O:13])=[O:7])([CH3:2])([CH3:3])[CH3:4]
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Komponenten

4

Edukt 2

HCID 76809N-((1,1-dimethylethoxy)carbonyl)-beta-alanineHCID 15546287(S)-N-[2-(2,3-dihydrobenzofuran-5-yl)-1-methylethyl]-N-ethyl-(piperidin-4-ylmethyl)amine

Produkt 1

HCID 54233503(S)-3-tert-Butoxycarbonylamino-1-[4-({[2-(2,3-dihydrobenzofuran-5-yl)-1-methylethyl]ethylamino}methyl)piperidin-1-yl]-propan-1-oneAusbeute 97,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344Dichloromethane
Lösungsmittel
2×

Versuchsvorschrift

To a solution of N-tert-butoxycarbonyl-β-alanine (0.31 grams, 165 mmole) in dichloromethane (5 ml) was added N,N′-carbonyldiimidazole (0.3 grams, 185 mmole). The reaction mixture was stirred at room temperature for 2 hours. To the reaction mixture was added a solution of (S)-N-[2-(2,3-dihydrobenzofuran-5-yl)-1-methylethyl]-N-ethyl-(piperidine-4-ylmethyl)amine (0.5 grams, 1.65 mmole) in dichloromethane (2 ml). The reaction mixture was stirred for 16 hours. The solvent was evaporated and the residue was purified by flash chromatography on silica gel using 2% methanol in dichloromethane containing 0.1% ammonium hydroxide. Appropriate fractions were combined and concentrated to give (S)-3-tert-butoxycarbonylamino-1-[4-({[2-(2,3-dihydrobenzofuran-5-yl)-1-methylethyl]-ethylamino}methyl)piperidin-1-yl]propan-1-one as a solid (0.76 grams, 97%).

Aufarbeitung

  1. stirringThe reaction mixture was stirred for 16 hours
  2. customThe solvent was evaporated
  3. customthe residue was purified by flash chromatography on silica gel using 2% methanol in dichloromethane containing 0.1% ammonium hydroxide
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-5ca099bd3998408abc74940048be0e87
Quelldatensatz
uspto-grants-2001_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06319920B1

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