2-Aminophenol → 5-Bromo-3',5'-diacetyl-N4-(2-hydroxyphenyl)-2'-deoxycytidine

HRID 1647922Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1647922
[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.C1CCN2C(=NCCC2)CC1.[NH2:55][C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][C:57]=1[OH:62]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Br:22][C:20]1[C:18]([NH:55][C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][C:57]=2[OH:62])=[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 58012-AminophenolHCID 8471TriethylamineHCID 130462-Mesitylenesulfonyl chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 22854693HCID 22854693, Verbindung

Produkt 1

HCID 677786545-Bromo-3',5'-diacetyl-N4-(2-hydroxyphenyl)-2'-deoxycytidine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 3',5'-diacetyl-5-bromo-2'-deoxyuridine (8.5 g; 21.7 mmol), methylene chloride (100 ml), triethylamine (8.8 g; 87 mmol) and DMAP (0.13 g) was added 2-mesitylsulfonyl chloride (9.5 g; 43.4 mmol). After stirring at room temperature for 18 h. DBU (6.6 g; 43.5 mmol) and 2-aminophenol (9.5 g; 87 mmol) were added and the solution was stirred for 1 hr. The reaction mixture was concentrated and the residue was partitioned between ethyl acetate and saturated sodium bicarbonate aq. solution. The organic layer was purified by flash column chromatography on silica gel to yield the title compound.

Aufarbeitung

  1. stirringthe solution was stirred for 1 hr
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was partitioned between ethyl acetate and saturated sodium bicarbonate aq. solution
  4. customThe organic layer was purified by flash column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-004151302df74bb4bca671f91235419b
Quelldatensatz
uspto-grants-1995_07
Patentnummer
US05434257

Notizen zur Reaktion

Wird geladen…