Water → (4R,9aR)-4-Methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2,6-dicarboxylic acid 2-tert-butyl ester 6-methyl ester

HRID 11923

Reaktionsgleichung

Reaktionsgleichung von HRID 11923
[C:1]([O:5][C:6]([N:8]1[CH2:20][C@@H:19]([CH3:21])[N:18]2[C@H:10]([CH2:11][C:12]3[C:17]2=[N:16][C:15](Br)=[CH:14][CH:13]=3)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.O.[C:31]([O:34][CH2:35]C)(=[O:33])C>CO.[Cl-].[Na+].O>[CH3:35][O:34][C:31]([C:15]1[N:16]=[C:17]2[C:12](=[CH:13][CH:14]=1)[CH2:11][C@H:10]1[N:18]2[C@H:19]([CH3:21])[CH2:20][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9]1)=[O:33]

Komponenten

7

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 86590113(4R,9aR)-6-bromo-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester2×

Produkt 1

HCID 67239630(4R,9aR)-4-Methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2,6-dicarboxylic acid 2-tert-butyl ester 6-methyl esterAusbeute 74,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

To a solution of 6.0 g (16.3 mmol) (4R,9aR)-6-bromo-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester (Example 5, intermediate b) in 60 ml methanol were added 0.57 g (0.8 mmol) and 3.4 ml (2.5 g, 24.4 mmol) triethylamine and the reaction mixture was stirred at 80 deg C. for 24 h under a carbon monoxide atmosphere of 40 bar. The suspension was cooled to room temperature, poured into a mixture of water, ethyl acetate and brine and was extracted with further portions of ethyl acetate. The combined organic layers were separated, dried over magnesium sulfate and filtered. The residue was purified by chromatography on silica gel (0.032–0.063 mm) to afford the product as a light yellow foam (74.4%).

Aufarbeitung

  1. extractionwas extracted with further portions of ethyl acetate
  2. customThe combined organic layers were separated
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customThe residue was purified by chromatography on silica gel (0.032–0.063 mm)

Quellen und Nachweise

ORD-Eintrag
ord-e8430ae839444098ab6a91097b86fa43
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07098337B2

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