3-Methyl-4-nitrobenzoic acid → N-(3-Methyl-4-nitrobenzoyl)serine methyl ester

HRID 1425106

Reaktionsgleichung

Reaktionsgleichung von HRID 1425106
Cl.[CH3:2][O:3][C:4](=[O:9])[C@H:5]([CH2:7][OH:8])[NH2:6].[CH3:10][C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][C:19]=1[N+:20]([O-:22])=[O:21])[C:14](O)=[O:15].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:9])[C@H:5]([CH2:7][OH:8])[NH:6][C:14](=[O:15])[C:13]1[CH:17]=[CH:18][C:19]([N+:20]([O-:22])=[O:21])=[C:11]([CH3:10])[CH:12]=1

Komponenten

7

Edukt 4

HCID 183703-Methyl-4-nitrobenzoic acidHCID 81531DiisopropylethylamineHCID 2723730L-Serine, methyl ester, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Produkt 1

HCID 67549024N-(3-Methyl-4-nitrobenzoyl)serine methyl esterAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

The same operation as in Example (102a) was performed using serine methyl ester hydrochloride (5.24 g, 33.7 mmol), 3-methyl-4-nitrobenzoic acid (6.1 g, 33.7 mmol), WSC hydrochloride (6.71 g, 35 mmol), DMAP (0.18 g, 1.5 mmol), N,N-diisopropylethylamine (4.52 g, 35 mmol) and dichloromethane (100 mL). The resulting residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane=1/4, 1/2, 2/1, 1/0) to obtain 8.35 g of the title compound as a light yellow solid (88%).

Aufarbeitung

  1. customThe resulting residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane=1/4, 1/2, 2/1, 1/0)

Quellen und Nachweise

ORD-Eintrag
ord-2e5e136740c443bcbc1eab2980ec0050
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08927588B2

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