octanamide

Conditions: temp:10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 135.03 g of Dimethyl Amine solution is charged at room temperature and cooled to 10±2° C., then Octanoyl Chloride obtained in EXAMPLE 4 is charged at 8 to 12° C. over a period of 2 hours, and the reaction mixture is stirred at 10 to 15° C. for 30 minutes and then stirred at room temperature for 1 hour and the upper organic layer is separated from lower aqueous layer and 29.80 g of Sodium Chloride (20% solution) is added to the organic layer. This organic layer is washed and 9.94 g of Sodium Sulphate is added to the organic layer to take up water, and the mixture is filtered to obtain crude Octanamide. stirred at room temperature for 1 hour the upper organic layer is separated from lower aqueous layer and 29.80 g of Sodium Chloride (20% solution) is added to the organic layer This organic layer is washed 9.94 g of Sodium Sulphate is added to the organic layer the mixture is filtered

Conditions: temp:10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 135.03 g of Dimethyl Amine solution is charged at room temperature and cooled to 10±2° C., then Octanoyl Chloride obtained in EXAMPLE 4 is charged at 8 to 12° C. over a period of 2 hours, and the reaction mixture is stirred at 10 to 15° C. for 30 minutes and then stirred at room temperature for 1 hour and the upper organic layer is separated from lower aqueous layer and 29.80 g of Sodium Chloride (20% solution) is added to the organic layer. This organic layer is washed and 9.94 g of Sodium Sulphate is added to the organic layer to take up water, and the mixture is filtered to obtain crude Octanamide. stirred at room temperature for 1 hour the upper organic layer is separated from lower aqueous layer and 29.80 g of Sodium Chloride (20% solution) is added to the organic layer This organic layer is washed 9.94 g of Sodium Sulphate is added to the organic layer the mixture is filtered

Conditions: temp:10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 135.03 g of Dimethyl Amine solution is charged at room temperature and cooled to 10±2° C., then Octanoyl Chloride obtained in EXAMPLE 4 is charged at 8 to 12° C. over a period of 2 hours, and the reaction mixture is stirred at 10 to 15° C. for 30 minutes and then stirred at room temperature for 1 hour and the upper organic layer is separated from lower aqueous layer and 29.80 g of Sodium Chloride (20% solution) is added to the organic layer. This organic layer is washed and 9.94 g of Sodium Sulphate is added to the organic layer to take up water, and the mixture is filtered to obtain crude Octanamide. stirred at room temperature for 1 hour the upper organic layer is separated from lower aqueous layer and 29.80 g of Sodium Chloride (20% solution) is added to the organic layer This organic layer is washed 9.94 g of Sodium Sulphate is added to the organic layer the mixture is filtered

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Compound 54 was prepared from octanamide and 4-(diethylamino)benzaldehyde using method 1. Yield: 68%. 1H NMR (400 MHz, DMSO) δ 8.21 (d, J=8.0 Hz, 2H), 7.07 (d, J=8.8 Hz, 2H), 6.61 (d, J=8.8 Hz, 2H), 6.42 (t, J=8.0 Hz, 1H), 3.29-3.31 (m, 4H), 2.06-2.14 (m, 4H), 1.47-1.50 (m, 4H), 1.08-1.24 (m, 16H), 1.06 (t, J=7.2 Hz, 6H), 0.94 (t, J=7.2 Hz, 6H). LC-MS (ESI): m/z 446.3 (M+H)+. HRMS (ESI) for C27H48N3O2 (MH+): calcd, 446.3741. found 446.3734.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Compound 54 was prepared from octanamide and 4-(diethylamino)benzaldehyde using method 1. Yield: 68%. 1H NMR (400 MHz, DMSO). δ 8.21 (d, J=8.0 Hz, 2H), 7.07 (d, J=8.8 Hz, 2H), 6.61 (d, J=8.8 Hz, 2H), 6.42 (t, J=8.0 Hz, 1H), 3.29-3.31 (m, 4H), 2.06-2.14 (m, 4H), 1.47-1.50 (m, 4H), 1.08-1.24 (m, 16H), 1.06 (t, J=7.2 Hz, 6H), 0.94 (t, J=7.2 Hz, 6H). LC-MS (ESI): m/z 446.3 (M+H)+. HRMS (ESI) for C27H48N3O2 (MH+): calcd, 446.3741. found 446.3734.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Synthesis of 5LO sequence 5′-GAA GTC ACT GGA ACG-3′ (SEQ ID NO:21) containing 2-octanoxyadenine at specific positions is described. A solution of N6-benzoyl-2′-deoxy-2-methyl-sulfonyladenosine, ethyl diisopropylamine, octanoylamine, and DMF is heated to 100° C. for 30 min and evaporated to dryness under reduced pressure. Recrystallization of the residue affords N6-benzoyl-2′-deoxyadenosine with the carbon chain in the 2-position. This material is converted by procedures of examples 107 and 108 above into its 5′-DMT-3′-β-cyanoethyldiisopropylphosphoramidite derivative which is inserted into the 5LO-sequence 5′-GAA GTC ACT GGA ACG (SEQ ID NO:21) via automated, solid phase DNA synthesis. Synthesis of 5LO sequence 5′-GAA GTC ACT GGA evaporated to dryness under reduced pressure Recrystallization of the residue