Ammonia → HCID 11069003, compound

HRID 1689651Notes

Reaction equation

HRID 1689651 reaction equation
[OH:1][C@H:2]1[C@H:6]2[O:7][CH2:8][C@:3]1([CH2:19][OH:20])[O:4][C@H:5]2[N:9]1[CH:17]=[N:16][C:15]2[C:10]1=[N:11][CH:12]=[N:13][C:14]=2[NH2:18].C[Si](Cl)(C)C.[C:26](Cl)(=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.N>N1C=CC=CC=1>[OH:1][C@H:2]1[C@H:6]2[O:7][CH2:8][C@:3]1([CH2:19][OH:20])[O:4][C@H:5]2[N:9]1[CH:17]=[N:16][C:15]2[C:10]1=[N:11][CH:12]=[N:13][C:14]=2[NH:18][C:26](=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 6397ChlorotrimethylsilaneHCID 7412Benzoyl chlorideHCID 44436074HCID 44436074, compound

Product 1

HCID 11069003HCID 11069003, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of nucleoside 61A (0.32 g, 1.15 mmol) in anhydrous pyridine (1 cm3) was added trimethylsilyl chloride (0.73 cm3, 5.73 mmol) and the mixture was stirred at room temperature for 20 min. Benzoyl chloride (0.67 cm3, 5.73 mmol) was added at 0° C., and the reaction mixture was stirred at room temperature for 2 h. The reaction mixture was cooled to 0° C. and ice-cold water (15.0 cm3) was added. After stiffing for 5 min, a 32% (w/w) aqueous solution of ammonia (1.5 cm3) was added and the mixture was stirred for 30 min. The mixture was evaporated to dryness and the residue was dissolved in water (25 cm3). After evaporation of the mixture under reduced pressure, the residue was purified by silica gel chromatography using dichloromethane/methanol (97:3, v/v) as eluent to give nucleoside 61B as a white solid material (0.55 g). FAB-MS m/z 384 [M+H]+.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 2 h
  2. temperatureThe reaction mixture was cooled to 0° C.
  3. waitAfter stiffing for 5 min
  4. stirringthe mixture was stirred for 30 min
  5. customThe mixture was evaporated to dryness
  6. dissolutionthe residue was dissolved in water (25 cm3)
  7. customAfter evaporation of the mixture under reduced pressure
  8. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-3e4ea16f173f4dfca34d0f82a05247e4
Source dataset
uspto-grants-2012_04
Patent number
US08153365B2

Reaction notes

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