tetramethylazanium;hydroxide;pentahydrate

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

Procedure: To a solution of 1.05 g of the product of step b) in 5 ml dimethylformamide are added 362 mg tetramethylammonium hydroxide pentahydrate. The mixture is stirred at room temperature 1 1/2 hours and then treated with 394 mg cinnamyl bromide. The mixture is stirred at room temperature 17 hours. The mixture is diluted with ice/water (about 50 ml) and extracted with diethyl ether. The extracts are washed with 10 ml aqueous 1N KHCO3 solution, dried (Na2SO4) and evaporated to give the heading compound as an oil. The mixture is stirred at room temperature 17 hours extracted with diethyl ether The extracts are washed with 10 ml aqueous 1N KHCO3 solution dried (Na2SO4) evaporated

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

Procedure: Tetramethylammonium hydroxide pentahydrate (1.7 g, 9.4 mmol) was added to a solution of the title product of Example 1 (2.0 g, 8.7 mmol) in 45 mL of anhydrous acetonitrile. After stirring for 4 hours at room temperature, methyl iodide (0.6 mL, 9.6 mmol) was added and the resulting milky solution stirred at room temperature. The solvent was removed by rotary evaporator and partioned between diethyl ether and water. The organic phase was washed with brine, dried over magnesium sulfate, filtered and concentrated to give the title compound (2.1 g) as a pale yellow liquid. The structure was supported by NMR, infrared spectroscopy, elemental analysis and mass spectroscopy. the resulting milky solution stirred at room temperature The solvent was removed by rotary evaporator The organic phase was washed with brine dried over magnesium sulfate filtered concentrated

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

Procedure: Reaction Scheme 6 illustratively shows the preparation of N-(12-methoxy-1-oxododecyl)-D-alanine, ethyl ester wherein N-(t-butyloxycarbonyl)-D-alanine (16) is treated with tetramethylammonium hydroxide pentahydrate in acetonitrile followed by the addition of ethyl iodide to form N-(t-butyloxycarbonyl)-D-alanine, ethyl ester (17) which in turn reacts with trifluoroacetic acid in methylene chloride to give the trifluoroacetate salt of D-alanine ethyl ester (18) which, when treated with 2-methoxydodecanoyl chloride (9) in methylene chloride, gives the desired fatty acid amino ester (19). Reaction Scheme 6

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

Procedure: To a solution of 1.05 g of the product of step b) in 5 ml dimethylformamide are added 362 mg tetramethyl ammonium hydroxide pentahydrate. The mixture is stirred at room temperature 11/2 hours and then treated with 394 mg cinnamyl bromide. The mixture is stirred at room temperature 17 hours. The mixture is diluted with ice/water (about 50 ml) and extracted with diethyl ether. The extracts are washed with 10 ml aqueous 1N KHCO3 solution, dried (Na2SO4) and evaporated to give the heading compound as an oil. The mixture is stirred at room temperature 17 hours extracted with diethyl ether The extracts are washed with 10 ml aqueous 1N KHCO3 solution dried (Na2SO4) evaporated

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

Procedure: 60 m moles(10.9 g) of tetramethylammonium hydroxide pentahydrate was added to a DMF solution of 60 m moles(3.6 g) of acetic acid, and stirred for one hour, then 50 m moles(23.1 g) of the above 4'-(10-bromodecyloxy)biphenyl-4-carboxylic acid ethyl ester was added thereto, and stirred for 12 hours. The reaction solution was ether extracted and concentrated, and then purified by column chromoatography, to obtain 15.4 g of 4'-(10-acetyloxydecyloxy)biphenyl-4-carboxylic acid ethyl ester. (yield: 70%) stirred for 12 hours extracted concentrated purified by column chromoatography

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

Procedure: 60 m moles(10.9 g) of tetramethylammonium hydroxide pentahydrate was added into a DMF solution of 60 m moles(3.6 g) of acetic acid, stirred for one hour, then 50 m moles(27.3 g) of the above 4'-(16-bromohexadecyloxy)biphenyl-4-carboxylic acid ethyl ester was added, and stirred for 12 hours. The reaction solution was ether extracted and concentrated, then purified by column chromatography to obtain 18.1 g of 4'-(16-acetyloxyhexadecyloxy)biphenyl-4-carboxylic acid ethyl ester. (yield: 69%) stirred for 12 hours extracted concentrated purified by column chromatography

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

Procedure: 60 m moles(10.9 g) of tetramethylammonium hydroxide pentahydrate was added to a DMF solution of 60 m moles(3.6 g) of acetic acid, and stirred for one hour, then 50 m moles(24.5 g) of the above 4'-(12-bromododecyloxy)biphenyl-4-carboxylic acid ethyl ester was added thereto, and stirred for 12 hours. After the reaction, the reaction solution was ether extracted. The extrate was concentrated, and then purified by column chromatography, to obtain 15.7 g of 4'-(12-acetyloxydodecyloxy)biphenyl-4-carboxylic acid ethyl ester [m.p. 80.1°-81.5° C⟧ (yield: 67%) stirred for 12 hours After the reaction extracted The extrate was concentrated purified by column chromatography

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

Procedure: One equivalent of tetramethyl ammonium hydroxide pentahydrate (18 g) was reacted with 0.1 equivalent of perfluorooctanoic acid (41 g) in water, to form tetra methylammonium perfluorooctanoate at a concentration of 5 percent by weight of the solution.

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

Procedure: One equivalent of tetramethyl ammonium hydroxide pentahydrate (18 g) was reacted with 0.1 equivalent of perfluorooctanoic acid (41 g) in water, to form tetra methylammonium perfluorooctanoate at a concentration of 5 percent by weight of the solution.

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

Procedure: Nitrobenzene (2 ml, 0.02 mole) was added via a syringe to a stirring solution containing 1.08 g (0.01 mole) of 1,4-phenylenediamine, 3.6 g (0.02 mole) of tetramethylammonium hydroxide pentahydrate in 2 ml of dimethylsulfoxide under nitrogen at 70° C. The solution was stirred at such condition for 4 hours. An aliquot was taken out for LC, MS, LC-MS analyses. N,N'-(4-nitrosophenyl)-1,4-phenylenediamine, N-(4-nitrophenyl)-N'-(4-nitrosophenyl)-1,4-phenylenediamine and N,N'-(4-nitrophenyl)-1,4-phenylenediamine were obtained.

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

Procedure: Nitrobenzene (2 ml, 0.02 mole) was added via a syringe to a stirring solution containing 1.08 g (0.01 mole) of 1,4-phenylenediamine, 3.6 g (0.02 mole) of tetramethylammonium hydroxide pentahydrate in 2 ml of dimethylsulfoxide under nitrogen at 70° C. The solution was stirred at such condition for 4 hours. An aliquot was taken out for LC, MS, LC-MS analyses. N,N'-(4-nitrosophenyl)-1,4-phenylenediamine, N-(4-nitrophenyl)-N'-(4-nitrosophenyl)-1,4-phenylenediamine and N,N'-(4-nitrophenyl)-1,4-phenylenediamine were obtained.

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

Procedure: Tetramethylammonium hydroxide pentahydrate (1.7 g, 9.4 mmol) was added to a solution of the title product of Example 1 (2.0 g, 8.7 mmol) in 45 mL of anhydrous acetonitrile. After stirring for 4 hours at room temperature, methyl iodide (0.6 mL, 9.6 mmol) was added and the resulting milky solution stirred at room temperature. The solvent was removed by rotary evaporator and partioned between diethyl ether and water. The organic phase was washed with brine, dried over magnesium sulfate, filtered and concentrated to give the title compound (2.1 g) as a pale yellow liquid. The structure was supported by NMR, infrared spectroscopy, elemental analysis and mass spectroscopy. the resulting milky solution stirred at room temperature The solvent was removed by rotary evaporator The organic phase was washed with brine dried over magnesium sulfate filtered concentrated