5-fluoro-1-[(4R,6R)-6-(hydroxymethyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]pyrimidine-2,4-dione → 5'-O-(5-morpholinopentanoyl)-5-fluorouridine

HRID 1759381

Reaktionsgleichung

Reaktionsgleichung von HRID 1759381
Cl.[O:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])[CH2:4][CH2:3]1.CC1(C)[O:23][CH:22]2[CH:18]([C@@H:19]([CH2:33]O)[O:20][C@H:21]2[N:24]2[C:30](=[O:31])[NH:29][C:27](=[O:28])[C:26]([F:32])=[CH:25]2)[O:17]1>N1C=CC=CC=1>[O:2]1[CH2:3][CH2:4][N:5]([CH2:8][CH2:9][CH2:10][CH2:11][C:12]([O:14][CH2:33][C@H:19]2[O:20][C@@H:21]([N:24]3[CH:25]=[C:26]([F:32])[C:27](=[O:28])[NH:29][C:30]3=[O:31])[C@H:22]([OH:23])[C@@H:18]2[OH:17])=[O:13])[CH2:6][CH2:7]1

Komponenten

4

Edukt 2

HCID 2008315-fluoro-1-[(4R,6R)-6-(hydroxymethyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]pyrimidine-2,4-dioneHCID 131371655-(Morpholin-4-yl)pentanoic acid hydrochloride

Produkt 1

HCID 228209795'-O-(5-morpholinopentanoyl)-5-fluorouridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

To a solution of 2.96 g (13.2 m-mol) of 5-morpholinopentanoic acid hydrochloride in pyridine (30 ml) was added 4.2 g (13.9 m-mol) of TPS, and the mixture was stirred for 15 minutes at room temperature. To this solution was added 2.00 g (6.62 m-mol) of 2',3'-O-isopropylidene-5-fluorouridine, and the mixture was stirred for 18 hours at room temperature. The reaction liquid was concentrated under reduced pressure and the residue was distributed in chloroform (50 ml) and an 8% aqueous solution of potassium carbonate (50 ml). The aqueous phase was extracted with chloroform (50 ml ×5) and the extracts were combined with the chloroform phase previously obtained. The chloroform phase was dried with Na2SO4 and concentrated and the residue was subjected to a separation-purification treatment by way of silica gel column chromatography (column size: 5×8 cm, developing solvents: chloroform and chloroform containing 2% methanol) whereby 1.17 g of 5'-O-(5-morpholinopentanoyl)-2',3'-O-isopropylidene-5-fluorouridine was obtained.

Aufarbeitung

  1. stirringthe mixture was stirred for 18 hours at room temperature
  2. customThe reaction liquid
  3. concentrationwas concentrated under reduced pressure
  4. extractionThe aqueous phase was extracted with chloroform (50 ml ×5)
  5. custompreviously obtained
  6. dry with materialThe chloroform phase was dried with Na2SO4
  7. concentrationconcentrated
  8. customwas obtained

Quellen und Nachweise

ORD-Eintrag
ord-4dd768277ddc4bfaa84c3a27647af9c5
Quelldatensatz
uspto-grants-1982_07
Patentnummer
US04340728

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