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

HRID 1167394노트

반응식

HRID 1167394 반응식
[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

참가 물질

8

반응물 5

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

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-086364cb27504556b9ed8ec81ff4fcfa
출처 데이터셋
uspto-grants-2003_09
특허 번호
US06617437B1

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