Triethylamine → (2R,4R)-4-Methoxy-2-(4-methoxycarbonyl-phenylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 2217477Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2217477
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][CH3:14])[CH2:10][C@@H:9]1[C:15]([OH:17])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:18][O:19][C:20](=[O:28])[C:21]1[CH:26]=[CH:25][C:24]([NH2:27])=[CH:23][CH:22]=1.CCOC1N(C(OCC)=O)C2C(=CC=CC=2)C=C1.C(N(CC)CC)C>C(Cl)(Cl)Cl.CCOC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][CH3:14])[CH2:10][C@@H:9]1[C:15](=[O:17])[NH:27][C:24]1[CH:23]=[CH:22][C:21]([C:20]([O:19][CH3:18])=[O:28])=[CH:26][CH:25]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 12082Methyl 4-aminobenzoateHCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 11459222(2R,4R)-1-[(tert-butoxy)carbonyl]-4-methoxypyrrolidine-2-carboxylic acid

Produkt 1

HCID 68808041(2R,4R)-4-Methoxy-2-(4-methoxycarbonyl-phenylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl esterAusbeute 100,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Into a solution of 6 (8.11 g, 33.0 mmol) in CHCl3 (200 mL) was added 4-amino-benzoic acid methyl ester (5.00 g, 33.0 mmol), EEDQ (9.81 g, 39.6 mmol), and triethylamine (6.9 mL, 49.6 mmol). The solution was stirred at reflux for 19 h before cooling to RT and adding EtOAc. The solution was washed sequentially with 1N HCl, 0.1N NaOH, water, and brine, before drying over MgSO4 and concentrating under reduced pressure to give 7 (12.50 g, 100%). MS: APCI (AP+): 379.3 (M)+, (AP−): 377.3 (M)−.

Aufarbeitung

  1. temperatureat reflux for 19 h
  2. washThe solution was washed sequentially with 1N HCl, 0.1N NaOH, water, and brine
  3. dry with materialbefore drying over MgSO4
  4. concentrationconcentrating under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-96f3c2fa9a264a4d896449eb54bb91e8
Quelldatensatz
uspto-grants-2008_08
Patentnummer
US07407972B2

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