Oxalyl chloride → Tert-butyl 2-(1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamido)acetate

HRID 13646

Reaktionsgleichung

Reaktionsgleichung von HRID 13646
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([C:12](Cl)=[O:13])[C:3]1=[O:15].CN1C2C(=CC=CC=2)C=C(C(O)=O)C1=O.C(Cl)(=O)C(Cl)=O.Cl.[NH2:38][CH2:39][C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41].C(N(C(C)C)CC)(C)C>ClCCl>[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([C:12]([NH:38][CH2:39][C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])=[O:13])[C:3]1=[O:15]

Komponenten

7

Edukt 5

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 2725036Glycine tert-butyl ester hydrochlorideHCID 124153511-Methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acidHCID 866158911-Methyl-2-oxo-1,2-dihydroquinoline-3-carbonyl chloride

Produkt 1

HCID 67388284Tert-butyl 2-(1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamido)acetateAusbeute 27 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

1-methyl-2-oxo-1,2-dihydroquinoline-3-carbonyl chloride, prepared from 1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid (Archiv der Pharmazie (1990), 323(2), 67-72) and oxalyl chloride, was added dropwise to a solution of tert-butyl 2-aminoacetate hydrochloride (0.041 g, 0.25 mmol), diisopropylethyl amine (0.086 ml, 0.49 mmol), in dichloromethane (1.00 ml), stirred at room temperature for 1 hr. The reaction mixture was diluted with dichloromethane, washed with water and dried over MgSO4 to afford tert-butyl 2-(1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamido)acetate in a 27% yield.

Aufarbeitung

  1. washwashed with water
  2. dry with materialdried over MgSO4

Quellen und Nachweise

ORD-Eintrag
ord-45ef108b719a4cb788350efe6b0aa700
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728130B2

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