5-(Tert-butyloxycarbonyl)-2-(4-fluorobenzyl)-8-hydroxy-6-methyl-2,3,4,4a,5,6-hexahydro-2,6-naphthyridine-1,7-dione → 2-(4-Fluorobenzyl)-8-hydroxy-6-methyl-2,3,4,4a,5,6-hexahydro-2,6-naphthyridine-1,7-dione-5-carboxylic acid

HRID 1436884Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1436884
C([O:5][C:6]([CH:8]1[N:17]([CH3:18])[C:16](=[O:19])[C:15]([OH:20])=[C:14]2[CH:9]1[CH2:10][CH2:11][N:12]([CH2:22][C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=1)[C:13]2=[O:21])=[O:7])(C)(C)C>C(O)(C(F)(F)F)=O.C(Cl)Cl>[F:29][C:26]1[CH:27]=[CH:28][C:23]([CH2:22][N:12]2[CH2:11][CH2:10][CH:9]3[C:14](=[C:15]([OH:20])[C:16](=[O:19])[N:17]([CH3:18])[CH:8]3[C:6]([OH:7])=[O:5])[C:13]2=[O:21])=[CH:24][CH:25]=1

Komponenten

4

Edukt 1

HCID 547137575-(Tert-butyloxycarbonyl)-2-(4-fluorobenzyl)-8-hydroxy-6-methyl-2,3,4,4a,5,6-hexahydro-2,6-naphthyridine-1,7-dione

Produkt 1

HCID 690691832-(4-Fluorobenzyl)-8-hydroxy-6-methyl-2,3,4,4a,5,6-hexahydro-2,6-naphthyridine-1,7-dione-5-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 6422Trifluoroacetic acidLösungsmittel2×

Versuchsvorschrift

A solution of 5-(tert-butyloxycarbonyl)-2-(4-fluorobenzyl)-8-hydroxy-6-methyl-2,3,4,4a,5,6-hexahydro-2,6-naphthyridine-1,7-dione, Diastereomer 1 from Example 4, (0.015 g, 0.037 mmol) in 50% TFA in CH2Cl2 (2.4 mL) was stirred at room temperature. After 1.3 hours, TFA acid (0.5 mL) was added to the reaction mixture. After 48 hours, the reaction mixture was concentrated under vacuum to give the title compound. ES MS M+1=349.

Aufarbeitung

  1. waitAfter 48 hours
  2. concentrationthe reaction mixture was concentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-73bc0118e28749b19840ae591e7a6f0c
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07619086B2

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