Potassium Carbonate → Di-tert-butyl (1R,2R,3S,4S,5R,6R)-2-(tert-butoxycarbonylamino)-3-[(3,4-dichlorophenyl)methoxy]-4-[(2-methyl-1,2,4-triazol-3-yl)sulfanyl]bicyclo[3.1.0]hexane-2,6-dicarboxylate

HRID 2172997Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2172997
[CH3:1][N:2]1[C:6](=[S:7])[N:5]=[CH:4][NH:3]1.C(=O)([O-])[O-].[K+].[K+].[C:14]([O:18][C:19]([NH:21][C@@:22]1([C:50]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])[C@H:27]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][C:33]([Cl:36])=[C:32]([Cl:37])[CH:31]=2)[C@H:26](OS(C)(=O)=O)[C@@H:25]2[C@H:23]1[C@H:24]2[C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])=[O:20])([CH3:17])([CH3:16])[CH3:15]>CN(C)C=O.[Cl-].[Na+].O>[C:14]([O:18][C:19]([NH:21][C@@:22]1([C:50]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])[C@H:27]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][C:33]([Cl:36])=[C:32]([Cl:37])[CH:31]=2)[C@@H:26]([S:7][C:6]2[N:2]([CH3:1])[N:3]=[CH:4][N:5]=2)[C@@H:25]2[C@H:23]1[C@H:24]2[C:43]([O:45][C:46]([CH3:48])([CH3:47])[CH3:49])=[O:44])=[O:20])([CH3:17])([CH3:15])[CH3:16]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 30381873H-1,2,4-Triazole-3-thione, 1,2-dihydro-2-methyl-HCID 86695975Di-tert-butyl (1S,2R,3S,4R,5R,6R)-2-[(tert-butoxycarbonyl)amino]-3-[(3,4-dichlorobenzyl)oxy]-4-[(methylsulfonyl)oxy]bicyclo[3.1.0]hexane-2,6-dicarboxylate

Produkt 1

HCID 67708365Di-tert-butyl (1R,2R,3S,4S,5R,6R)-2-(tert-butoxycarbonylamino)-3-[(3,4-dichlorophenyl)methoxy]-4-[(2-methyl-1,2,4-triazol-3-yl)sulfanyl]bicyclo[3.1.0]hexane-2,6-dicarboxylateAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Add 2-methyl-1H-1,2,4-triazole-3-thione (0.126 g, 1.09 mmol) and potassium carbonate (0.35 g, 2.52 mmol) to a solution of di-tert-butyl (1S,2R,3S,4R,5R,6R)-2-[(tert-butoxycarbonyl)amino]-3-[(3,4-dichlorobenzyl)oxy]-4-[(methylsulfonyl)oxy]bicyclo[3.1.0]hexane-2,6-dicarboxylate (0.80 g, 0.84 mmol) in dimethylformamide (1.68 mL. After heating for 2 days at 80° C., pour the solution into brine and extract with ethyl acetate three times, dry the combined organic phases with sodium sulfate, filter and concentrate under reduced pressure. Purify by flash chromatography eluting with 10% ethyl acetate/CH2Cl2 to yield the title compound as an oil (0.576 g, 0.84 mmol, 100%). MS (m/z): 685/687/689 (M+1).

Aufarbeitung

  1. extractionextract with ethyl acetate three times
  2. dry with materialdry the combined organic phases with sodium sulfate
  3. filtrationfilter
  4. concentrationconcentrate under reduced pressure
  5. customPurify by flash chromatography
  6. washeluting with 10% ethyl acetate/CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-e7dcbeab7bf1470882595232f03fb5f6
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09056844B2

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