Triethylamine → 2-[4-(4-Acetoxypiperidin-1-carbonyl)benzyl]-3-isopropylmaleic acid dimethyl ester

HRID 418760Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 418760
[CH3:1][O:2][C:3](=[O:23])/[C:4](/[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20](O)=[O:21])=[CH:16][CH:15]=1)=[C:5](/[CH:10]([CH3:12])[CH3:11])\[C:6]([O:8][CH3:9])=[O:7].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.Cl.[C:47]([O:50][CH:51]1[CH2:56][CH2:55][NH:54][CH2:53][CH2:52]1)(=[O:49])[CH3:48].C(N(CC)CC)C>ClCCl.O>[CH3:1][O:2][C:3](=[O:23])/[C:4](/[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([N:54]2[CH2:55][CH2:56][CH:51]([O:50][C:47](=[O:49])[CH3:48])[CH2:52][CH2:53]2)=[O:21])=[CH:16][CH:15]=1)=[C:5](/[CH:10]([CH3:11])[CH3:12])\[C:6]([O:8][CH3:9])=[O:7]

Komponenten

8

Edukt 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 12694334Piperidin-4-yl acetate hydrochlorideHCID 666486782-(4-Carboxybenzyl)-3-isopropylmaleic acid dimethyl ester

Produkt 1

HCID 597065112-[4-(4-Acetoxypiperidin-1-carbonyl)benzyl]-3-isopropylmaleic acid dimethyl esterAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 2-(4-carboxybenzyl)-3-isopropylmaleic acid dimethyl ester (10.3 mg, 0.0322 mmol) in dichloromethane (500 μL) were added 1-hydroxybenzotriazole (13.3 mg, 0.0965 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (20.8 mg, 0.109 mol), piperidin-4-yl acetate hydrochloride (28.8 mg, 0.161 mmol) and triethylamine (14.6 mg, 0.145 mmol) with stirring under ice cooling. After stirring at room temperature for 1 h, the reaction mixture was diluted with water to separate the phases. The aqueous layer was extracted again with ethyl acetate, and the combined organic layer was concentrated under reduced pressure and the residue thus obtained was subjected to silica gel column chromatography (hexane-ethyl acetate1:2) to give 11.1 mg of the title compound as a solid (yield: 78%).

Aufarbeitung

  1. stirringAfter stirring at room temperature for 1 h
  2. customto separate the phases
  3. extractionThe aqueous layer was extracted again with ethyl acetate
  4. concentrationthe combined organic layer was concentrated under reduced pressure
  5. customthe residue thus obtained

Quellen und Nachweise

ORD-Eintrag
ord-0220469dc0634d2ea3dafad27955edad
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08093294B2

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