Triethylamine → 5-Bromo-3',5'-diacetyl-N4-(2-hydroxy-m-nitrophenyl)-2'-deoxycytidine

HRID 1647923Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1647923
[C:1]([C@@:4]1([OH:23])[C@@H:8]([CH:9]([C:11](=[O:13])[CH3:12])[OH:10])[O:7][C@@H:6]([N:14]2[CH:21]=[C:20]([Br:22])[C:18](=O)[NH:17][C:15]2=[O:16])[CH2:5]1)(=[O:3])[CH3:2].C(N(CC)CC)C.C1(C)C=C(C)C=C(C)C=1S(Cl)(=O)=[O:40].C1CCN2C(=NCCC2)CC1.[NH2:55][C:56]1[CH:61]=[C:60]([N+:62]([O-:64])=[O:63])[CH:59]=[CH:58][C:57]=1O>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Br:22][C:20]1[C:18]([NH:55][C:56]2[CH:57]=[CH:58][CH:59]=[C:60]([N+:62]([O-:64])=[O:63])[C:61]=2[OH:40])=[N:17][C:15](=[O:16])[N:14]([CH:21]=1)[C@@H:6]1[O:7][C@H:8]([CH:9]([C:11](=[O:13])[CH3:12])[OH:10])[C@@:4]([C:1](=[O:3])[CH3:2])([OH:23])[CH2:5]1

Komponenten

8

Edukt 5

HCID 8471TriethylamineHCID 130462-Mesitylenesulfonyl chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 36133892-Amino-4-NitrophenolHCID 22854693HCID 22854693, Verbindung

Produkt 1

HCID 697436245-Bromo-3',5'-diacetyl-N4-(2-hydroxy-m-nitrophenyl)-2'-deoxycytidine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 3',5'-diacetyl-5-bromo-2'-deoxyuridine (4.8 g; 12 mmol), methylene chloride (50 ml), triethylamine (5.0 g; 50 mmol) and DMAP (0.10 g) was added 2-mesitylsulfonyl chloride (5.2 g; 24 mmol). After stirring at room temperature for 4 h., DBU (3.6 g; 24 mmol) and 2-amino-4-nitrophenol (7.4 g; 48 mmol) were added and the solution was stirred for 3 h. The reaction mixture was concentrated and the residue was partitioned between ethyl acetate and saturated sodium bicarbonate. The organic layer was purified by flash column chromatography on silica gel. The isolated product had some impurity and was triturated with ethyl acetate. The yellowish precipitate was filtered off and washed with methylene chloride to yield the title compound.

Aufarbeitung

  1. stirringthe solution was stirred for 3 h
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was partitioned between ethyl acetate and saturated sodium bicarbonate
  4. customThe organic layer was purified by flash column chromatography on silica gel
  5. customwas triturated with ethyl acetate
  6. filtrationThe yellowish precipitate was filtered off
  7. washwashed with methylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-331a809738514f6e97d3f9462db22bf6
Quelldatensatz
uspto-grants-1995_07
Patentnummer
US05434257

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