Dimethylformamide → (S)-2-[(4-Benzyloxycarbonylmethoxy-quinoline-2-carbonyl)-amino]-pentanedioic acid 5-tert-butyl ester 1-methyl ester

HRID 1185482Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1185482
[CH3:1][O:2][C:3](=[O:28])[C@@H:4]([NH:14][C:15]([C:17]1[CH:26]=[C:25]([OH:27])[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]=1)=[O:16])[CH2:5][CH2:6][C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].CN(C=O)C.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:40]([O:47][C:48](=[O:51])[CH2:49]Br)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>O>[CH3:1][O:2][C:3](=[O:28])[C@@H:4]([NH:14][C:15]([C:17]1[CH:26]=[C:25]([O:27][CH2:49][C:48]([O:47][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)=[O:51])[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]=1)=[O:16])[CH2:5][CH2:6][C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 62576Benzyl bromoacetateHCID 178501467HCID 178501467, Verbindung

Produkt 1

HCID 68600712(S)-2-[(4-Benzyloxycarbonylmethoxy-quinoline-2-carbonyl)-amino]-pentanedioic acid 5-tert-butyl ester 1-methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 6.5 g of (S)-2-[(4-Hydroxy-quinoline-2-carbonyl)-amino]-pentanedioic acid 5-tert-butyl ester 1-methyl ester 50 ml of DMF, 6.5 g of cesium carbonate and 4.2 g of Bromo-acetic acid benzyl ester was added and stirred for 16 h. Then, the reaction mixture was diluted with water and extracted with DCM (3×150 ml). The combined organic phases were dried over MgSO4 and the solvents were removed under reduced pressure. The crude product was used in the next reaction step. Yield: 8.9 g.

Aufarbeitung

  1. extractionextracted with DCM (3×150 ml)
  2. dry with materialThe combined organic phases were dried over MgSO4
  3. customthe solvents were removed under reduced pressure
  4. customThe crude product was used in the next reaction step

Quellen und Nachweise

ORD-Eintrag
ord-7a6bafbf003845d49acb08dafef54bde
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08669266B2

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