trimethylphosphine THF → (1R,2R,3R,5R,6R)-2-amino-3-(3,4-dichlorobenzyloxy)-6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid 6-(2-aminoethyl)ester

HRID 2423370Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2423370
CP(C)C.O1CCCC1.[N:10]([CH2:13][CH2:14][O:15][C:16]([C@:18]1([F:38])[C@@H:23]2[C@H:19]1[CH2:20][C@@H:21]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][C:33]([Cl:36])=[C:32]([Cl:37])[CH:31]=1)[C@@:22]2([NH2:27])[C:24]([OH:26])=[O:25])=[O:17])=[N+]=[N-]>O1CCCC1.O>[NH2:10][CH2:13][CH2:14][O:15][C:16]([C@:18]1([F:38])[C@@H:23]2[C@H:19]1[CH2:20][C@@H:21]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][C:33]([Cl:36])=[C:32]([Cl:37])[CH:31]=1)[C@@:22]2([NH2:27])[C:24]([OH:26])=[O:25])=[O:17]

Komponenten

5

Edukt 2

HCID 86589763trimethylphosphine THFHCID 86610093(1R,2R,3R,5R,6R)-2-amino-3-(3,4-dichlorobenzyloxy)-6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid 6-(2-azidoethyl)ester

Produkt 1

HCID 66628581(1R,2R,3R,5R,6R)-2-amino-3-(3,4-dichlorobenzyloxy)-6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid 6-(2-aminoethyl)esterAusbeute 35,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

20 μL of a 1M trimethylphosphine/tetrahydrofuran solution was added to 6 mg of (1R,2R,3R,5R,6R)-2-amino-3-(3,4-dichlorobenzyloxy)-6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid 6-(2-azidoethyl)ester dissolved in a mixture of 0.15 mL of tetrahydrofuran and 0.02 mL of water at room temperature, and the mixture was stirred for 13 hours. After the solvent was distilled under reduced pressure, the residue was purified by reverse phase column chromatography (Wako gel 50C18 (made by Wako Pure Chemical Industries Ltd.), eluent: water to a 50% aqueous solution of acetonitrile), and the obtained solids were further washed with tetrahydrofuran, thereby yielding 2 mg of (1R,2R,3R,5R,6R)-2-amino-3-(3,4-dichlorobenzyloxy)-6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid 6-(2-aminoethyl)ester.

Aufarbeitung

  1. distillationAfter the solvent was distilled under reduced pressure
  2. customthe residue was purified by reverse phase column chromatography (Wako gel 50C18 (made by Wako Pure Chemical Industries Ltd.), eluent
  3. washwater to a 50% aqueous solution of acetonitrile), and the obtained solids were further washed with tetrahydrofuran

Quellen und Nachweise

ORD-Eintrag
ord-7007e9752be845b4ad054fc7cdcfc199
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07960579B2

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