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

HRID 1167394ノート

反応式

HRID 1167394 の反応式
[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

参加物

8

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

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-amino4-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 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.

後処理

  1. stirringthe solution was stirred for 3 h
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was partitioned between ethyl acetate 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

出典と根拠

ORDレコード
ord-086364cb27504556b9ed8ec81ff4fcfa
出典データセット
uspto-grants-2003_09
特許番号
US06617437B1

反応ノート

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