Water → HCID 60201199, Verbindung

HRID 241531

Reaktionsgleichung

Reaktionsgleichung von HRID 241531
[CH:1]1[C:7]([NH2:8])=[N:6][C:4](=[O:5])[N:3]([C@@H:9]2[O:13][C@H:12]([CH2:14][OH:15])[C@@H:11]([OH:16])[C:10]2([F:18])[F:17])[CH:2]=1.Cl.[CH2:20]([O:32][C:33]([C:35]1[C:36]([C:41](O)=[O:42])=[N:37][CH:38]=[CH:39][N:40]=1)=[O:34])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31].F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1.O>CN(C)C1C=CN=CC=1.CN(C)C=O>[CH2:20]([O:32][C:33]([C:35]1[C:36]([C:41](=[O:42])[NH:8][C:7]2[CH:1]=[CH:2][N:3]([C@H:9]3[C:10]([F:17])([F:18])[C@H:11]([OH:16])[C@@H:12]([CH2:14][OH:15])[O:13]3)[C:4](=[O:5])[N:6]=2)=[N:37][CH:38]=[CH:39][N:40]=1)=[O:34])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]

Komponenten

7

Edukt 4

HCID 962WaterHCID 60749Gemcitabine HydrochlorideHCID 2724699PyBOPHCID 667719023-(Dodecyloxycarbonyl)pyrazine-2-carboxylic acid

Produkt 1

HCID 60201199HCID 60201199, VerbindungAusbeute 23,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Gemcitabine hydrochloride (500 mg, 1.67 mmol), 3-(dodecyloxycarbonyl)pyrazine-2-carboxylic acid (674 mg, 2.01 mmol), (Benzotriazol-1-yl-oxy)tripyrrolidinophosphonium hexafluorophosphate (955 mg, 1.84 mmol), and 4-dimethylaminopyridine (244 mg, 2.0 mmol) were dissolved in N,N-dimethylformamide (10 mL) and stirred at room temperature overnight. The reaction mixture was poured into water, then extracted three times with ethyl acetate. The isolated organic phase was dried with anhydrous Na2SO4. The solvent was removed by vaporizing under reduced pressure. The residue was purified by silica column chromatography (developing agent; dichloromethane/methanol=40/1) to produce 225.7 mg of dodecyl-3-((1-((2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)carbamoyl)pyrazine-2-carboxylate. LC purity 98% (UV 254). LC-MS m/z 582 [M+H]+, (molecular formula: C27H37F2N5O7, molecular weight: 581). The structure and characterization data of the compound were shown in Table 1.

Aufarbeitung

  1. extractionextracted three times with ethyl acetate
  2. dry with materialThe isolated organic phase was dried with anhydrous Na2SO4
  3. customThe solvent was removed
  4. customThe residue was purified by silica column chromatography (developing agent; dichloromethane/methanol=40/1)

Quellen und Nachweise

ORD-Eintrag
ord-df1365858c024896b155249609c159b1
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08653048B2

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