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

HRID 1647922ノート

反応式

HRID 1647922 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.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

参加物

8

反応物 5

HCID 58012-AminophenolHCID 8471TriethylamineHCID 130462-Mesitylenesulfonyl chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 22854693HCID 22854693、化合物

生成物 1

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

後処理

  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

出典と根拠

ORDレコード
ord-004151302df74bb4bca671f91235419b
出典データセット
uspto-grants-1995_07
特許番号
US05434257

反応ノート

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