Triphenylphosphine → 4-((R)-1-Benzyloxycarbonyl-ethoxy)-7-methyl-quinoline-2-carboxylic acid methyl ester

HRID 1185558Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1185558
Cl.[CH3:2][O:3][C:4]([C:6]1[CH:15]=[C:14]([OH:16])[C:13]2[C:8](=[CH:9][C:10]([CH3:17])=[CH:11][CH:12]=2)[N:7]=1)=[O:5].[CH2:18]([O:25][C:26](=[O:30])[C@H:27]([CH3:29])O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1.O>[CH3:2][O:3][C:4]([C:6]1[CH:15]=[C:14]([O:16][C@@H:27]([C:26]([O:25][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:30])[CH3:29])[C:13]2[C:8](=[CH:9][C:10]([CH3:17])=[CH:11][CH:12]=2)[N:7]=1)=[O:5]

Komponenten

7

Edukt 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 11052238benzyl (2S)-2-hydroxypropanoateHCID 178498501HCID 178498501, Verbindung

Produkt 1

HCID 685993014-((R)-1-Benzyloxycarbonyl-ethoxy)-7-methyl-quinoline-2-carboxylic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 1.00 g 4-Hydroxy-7-methyl-quinoline-2-carboxylic acid methyl ester hydrochloride and 0.83 g benzyl-L-lactate in 30 ml THF were added 1.81 g triphenylphosphine and 1.20 g diethylazodicarboxylate. After 2 h LCMS indicated complete conversion and water was added to the reaction mixture which was subsequently extracted with ethyl acetate. The residue obtained after evaporation of the solvent was purified by flash chromatography on silica using an ethyl acetate/heptane gradient. Yield: 1.80 g.

Aufarbeitung

  1. extractionwas subsequently extracted with ethyl acetate
  2. customThe residue obtained
  3. customafter evaporation of the solvent
  4. customwas purified by flash chromatography on silica using an ethyl acetate/heptane gradient

Quellen und Nachweise

ORD-Eintrag
ord-c70cc9f1ae454041ba3df0e844b7755f
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08669266B2

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