Triphenylphosphine → 4-((S)-2-{[4-((R)-1-Benzyloxycarbonyl-ethoxy)-7-methyl-quinoline-2-carbonyl]-amino}-4-tert-butoxycarbonyl-butyryl)-piperazine-1-carboxylic acid butyl ester

HRID 1185568Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1185568
[CH2:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:40])[C@@H:15]([NH:25][C:26]([C:28]2[CH:37]=[C:36]([OH:38])[C:35]3[C:30](=[CH:31][C:32]([CH3:39])=[CH:33][CH:34]=3)[N:29]=2)=[O:27])[CH2:16][CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:10][CH2:9]1)=[O:7])[CH2:2][CH2:3][CH3:4].[CH2:41]([O:48][C:49](=[O:53])[C@H:50]([CH3:52])O)[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1.O>[CH2:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14](=[O:40])[C@@H:15]([NH:25][C:26]([C:28]2[CH:37]=[C:36]([O:38][C@@H:50]([C:49]([O:48][CH2:41][C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)=[O:53])[CH3:52])[C:35]3[C:30](=[CH:31][C:32]([CH3:39])=[CH:33][CH:34]=3)[N:29]=2)=[O:27])[CH2:16][CH2:17][C:18]([O:20][C:21]([CH3:23])([CH3:22])[CH3:24])=[O:19])[CH2:12][CH2:13]1)=[O:7])[CH2:2][CH2:3][CH3:4]

Komponenten

7

Edukt 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 11052238benzyl (2S)-2-hydroxypropanoateHCID 178452369HCID 178452369, Verbindung

Produkt 1

HCID 685996044-((S)-2-{[4-((R)-1-Benzyloxycarbonyl-ethoxy)-7-methyl-quinoline-2-carbonyl]-amino}-4-tert-butoxycarbonyl-butyryl)-piperazine-1-carboxylic acid butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 2 g 4-{(S)-4-tert-Butoxycarbonyl-2-[(4-hydroxy-7-methyl-quinoline-2-carbonyl)-amino]-butyryl}-piperazine-1-carboxylic acid butyl ester and 647 mg benzyl-L-lactate in 25 ml THF were added 1.4 g triphenylphosphine and 938 mg diethylazodicarboxylate. After stirring for 16 h at RT 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: 1.7 g.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-bd5d552e38be48c49683f2e5e7209bac
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08669266B2

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