3-Methoxy-4-nitrobenzoic acid → N-(3-Methoxy-4-nitrobenzoyl)threonine methyl ester

HRID 43609

Reaktionsgleichung

Reaktionsgleichung von HRID 43609
Cl.[CH3:2][O:3][C:4](=[O:10])[C@H:5]([C@@H:7]([CH3:9])[OH:8])[NH2:6].[CH3:11][O:12][C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][C:21]=1[N+:22]([O-:24])=[O:23])[C:16](O)=[O:17].CCN=C=NCCCN(C)C.Cl.C(N(CC)C(C)C)(C)C>CN(C1C=CN=CC=1)C.ClCCl>[CH3:2][O:3][C:4](=[O:10])[C@H:5]([C@@H:7]([CH3:9])[OH:8])[NH:6][C:16](=[O:17])[C:15]1[CH:19]=[CH:20][C:21]([N+:22]([O-:24])=[O:23])=[C:13]([O:12][CH3:11])[CH:14]=1

Komponenten

7

Edukt 4

HCID 787643-Methoxy-4-nitrobenzoic acidHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2734893Methyl L-threoninate hydrochloride

Produkt 1

HCID 67549208N-(3-Methoxy-4-nitrobenzoyl)threonine methyl esterAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

The same operation as in Example (102a) was performed using threonine methyl ester hydrochloride (2.88 g, 17 mmol), 3-methoxy-4-nitrobenzoic acid (3 g, 15.2 mmol), WSC hydrochloride (3.83 g, 20 mmol), DMAP (0.18 g, 1.5 mmol), N,N-diisopropylethylamine (2.58 g, 20 mmol) and dichloromethane (40 mL). The resulting residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane=1/2, 1/1, 2/1, 1/0) to obtain 4.49 g of the title compound as a light yellow amorphous solid (95%).

Aufarbeitung

  1. customThe resulting residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane=1/2, 1/1, 2/1, 1/0)

Quellen und Nachweise

ORD-Eintrag
ord-e340d1576ca54290a3f1d7e443e7d790
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536197B2

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