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

HRID 1063771Notes

Reaction equation

HRID 1063771 reaction equation
[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

Participants

8

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-85e9a7c1058d43f48801f4d37b0b3d19
Source dataset
uspto-grants-2005_11
Patent number
US06967079B2

Reaction notes

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