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

HRID 1647922Notes

Reaction equation

HRID 1647922 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.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

Participants

8

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-004151302df74bb4bca671f91235419b
Source dataset
uspto-grants-1995_07
Patent number
US05434257

Reaction notes

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