Triethylamine → HCID 69960946, compound

HRID 963602Notes

Reaction equation

HRID 963602 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].[CH2:24](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[C:57]([OH:66])=[CH:58][C:59]2[C:64]([CH:65]=1)=[CH:63]C=CC=2>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Br:22][C:20]1[C:18]([NH:55][C:56]2[CH:65]=[C:64]([CH3:63])[CH:59]=[C:58]([CH3:24])[C:57]=2[OH:66])=[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 794493-Amino-2-naphtholHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 22854693HCID 22854693, compound

Product 1

HCID 69960946HCID 69960946, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3',5'-diacetyl-5bromo-2'-deoxyuridine (4.0 g; 10 mmol), methylene chloride (50 ml), triethylamine (4.0 g; 40 mmol) and DMAP (0.1 g) was added 2-mesitylsulfonyl chloride (4.4 g; 20 mmol). After stirring at room temperature for 6 h. DBU (3.0 g; 20 mmol) and 3-amino-2-naphthol (6.4 g; 40 mmol) were added and the solution was stirred for 4 h. at room temperature. The reaction mixture was concentrated, the residue was dissolved in ethyl acetate and washed with saturated sodium bicarbonate aq. solution, but the title compound was precipitated from solution. The precipitates were filtered off and washed thoroughly with ethyl acetate, then methylene chloride, and dried. A small quantity of title compound also was obtained from the filtrate.

Workup

  1. stirringthe solution was stirred for 4 h. at room temperature
  2. concentrationThe reaction mixture was concentrated
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washwashed with saturated sodium bicarbonate aq. solution
  5. customthe title compound was precipitated from solution
  6. filtrationThe precipitates were filtered off
  7. washwashed thoroughly with ethyl acetate
  8. dry with materialmethylene chloride, and dried

Sources & evidence

ORD record
ord-c279eadcc1544c159562ed54ea66998a
Source dataset
uspto-grants-1998_06
Patent number
US05763588

Reaction notes

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