1,3-dioxolan-4-ylmethanol

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

Procedure: A mixture of 104 g of glycerol formal, 152 g of methyl 5-norbornene-2-carboxylate, 2.0 g of sodium methoxide and 300 ml of toluene was heated under reflux for 5 hours while gradually distilling off methanol formed during the reaction. After cooling, the reaction solution was washed with saturated sodium bicarbonate water, dried over anhydrous sodium sulfate, and concentrated in vacuum. It was further purified by vacuum distillation, obtaining 209 g of a mixture of (1,3-dioxolan-4-yl)methyl 5-norbornene-2-carboxylate and 1,3-dioxan-5-yl 5-norbornene-2-carboxylate (boiling point 111-115° C./530 Pa, yield 93%). was heated under reflux for 5 hours while gradually distilling off methanol formed during the reaction After cooling the reaction solution was washed with saturated sodium bicarbonate water dried over anhydrous sodium sulfate concentrated in vacuum It was further purified by vacuum distillation

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

Procedure: To a mixture of 104 g of glycerol formal, 111 g of triethylamine and 300 ml of toluene, 157 g of 5-norbornene-2-carbonyl chloride was added over one hour at 20° C. After 5 hours of stirring, 200 ml of water was added to stop the reaction and the mixture was allowed to separate. The organic layer was washed with water and saturated sodium chloride water, dried over anhydrous sodium sulfate, and concentrated in vacuum. It was further purified by vacuum distillation, obtaining 213 g of a mixture of (1,3-dioxolan-4-yl)methyl 5-norbornene-2-carboxylate and 1,3-dioxan-5-yl 5-norbornene-2-carboxylate (boiling point 111-115° C./530 Pa, yield 95%). was added over one hour at 20° C the reaction to separate The organic layer was washed with water and saturated sodium chloride water dried over anhydrous sodium sulfate concentrated in vacuum It was further purified by vacuum distillation

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

Procedure: A mixture of 104 g of glycerol formal, 152 g of methyl 5-norbornene-2-carboxylate, 2.0 g of sodium methoxide and 300 ml of toluene was heated under reflux for 5 hours while gradually distilling off methanol formed during the reaction. After cooling, the reaction solution was washed with saturated sodium bicarbonate water, dried over anhydrous sodium sulfate, and concentrated in vacuum. It was further purified by vacuum distillation, obtaining 209 g of a mixture of (1,3-dioxolan-4-yl)methyl 5-norbornene-2-carboxylate and 1,3-dioxan-5-yl 5-norbornene-2-carboxylate (boiling point 111-115° C./530 Pa, yield 93%). was heated under reflux for 5 hours while gradually distilling off methanol formed during the reaction After cooling the reaction solution was washed with saturated sodium bicarbonate water dried over anhydrous sodium sulfate concentrated in vacuum It was further purified by vacuum distillation

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

Procedure: A mixture of 104 g of glycerol formal, 152 g of methyl 5-norbornene-2-carboxylate, 2.0 g of sodium methoxide and 300 ml of toluene was heated under reflux for 5 hours while gradually distilling off methanol formed during the reaction. After cooling, the reaction solution was washed with saturated sodium bicarbonate water, dried over anhydrous sodium sulfate, and concentrated in vacuum. It was further purified by vacuum distillation, obtaining 209 g of a mixture of (1,3-dioxolan-4-yl)methyl 5-norbornene-2-carboxylate and 1,3-dioxan-5-yl 5-norbornene-2-carboxylate (boiling point 111-115° C./530 Pa, yield 93%). was heated under reflux for 5 hours while gradually distilling off methanol formed during the reaction After cooling the reaction solution was washed with saturated sodium bicarbonate water dried over anhydrous sodium sulfate concentrated in vacuum It was further purified by vacuum distillation

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

Procedure: To a mixture of 104 g of glycerol formal, 111 g of triethylamine and 300 ml of toluene, 157 g of 5-norbornene-2-carbonyl chloride was added over one hour at 20° C. After 5 hours of stirring, 200 ml of water was added to stop the reaction and the mixture was allowed to separate. The organic layer was washed with water and saturated sodium chloride water, dried over anhydrous sodium sulfate, and concentrated in vacuum. It was further purified by vacuum distillation, obtaining 213 g of a mixture of (1,3-dioxolan-4-yl)methyl 5-norbornene-2-carboxylate and 1,3-dioxan-5-yl 5-norbornene-2-carboxylate (boiling point 111-115° C./530 Pa, yield 95%). was added over one hour at 20° C the reaction to separate The organic layer was washed with water and saturated sodium chloride water dried over anhydrous sodium sulfate concentrated in vacuum It was further purified by vacuum distillation

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

Procedure: The NMP or dimethylacetamide, citric acid, propylene glycol, and approximately 90% of the PEG 300 or glycerol formal required for each formulation were charged to the compounding vessel and mixed well. The florfenicol and flunixin meglumine were added with mixing until all solids were dissolved. The volume was adjusted with the remaining PEG 300 or glycerol formal. were charged to the compounding vessel mixed well with mixing until all solids were dissolved

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

Procedure: The NMP or dimethylacetamide, citric acid, propylene glycol, and approximately 90% of the PEG 300 or glycerol formal required for each formulation were charged to the compounding vessel and mixed well. The florfenicol and flunixin meglumine were added with mixing until all solids were dissolved. The volume was adjusted with the remaining PEG 300 or glycerol formal. were charged to the compounding vessel mixed well with mixing until all solids were dissolved

Conditions: temp:75.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of glycerol formal (0.729 g, 7.0 mmol) in THF (3 ml) at room temperature is added dropwise a solution of lithium bis(trimethylsilyl)amide (1.0 M in hexanes)(3.50 ml, 3.50 mmol). The reaction mixture is stirred for 15 minutes and then is treated with 3-amino-5-chloro-6-methanesulfinyl-4-methyl-thieno[2,3-b]pyridine-2-carboxylic acid cyclopropylamide (0.345 g, 1.00 mmol). The reaction mixture is heated at 75° C. in a sealed tube for 1.5 hours, cooled to room temperature, and then quenched by the addition of water (10 ml). The reaction mixture is transferred to an erlenmeyer flask and diluted to 75 ml with water. The mixture is cooled to 0° C. and stirred. During this time, a white precipitate is formed. This solid is collected by filtration and slurried in a 2:1 EtOAc:hexane mixture. This slurry is stirred for 10 minutes, filtered, and the collected solid is placed in the vacuum oven to dry (60° C. for 16 hours). This affords the title compound as a white solid (0.195 g, 51%). Mass (m/z): 384.1 (M++1), 382.1 (M+−1). cooled to room temperature quenched by the addition of water (10 ml) The reaction mixture is transferred to an erlenmeyer flask diluted to 75 ml with water The mixture is cooled to 0° C. stirred During this time, a white precipitate is formed This solid is collected by filtration This slurry is stirred for 10 minutes filtered to dry (60° C. for 16 hours)

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

Procedure: A mixture of 104 g of glycerol formal, 152 g of methyl 5-norbornene-2-carboxylate, 2.0 g of sodium methoxide and 300 ml of toluene was heated under reflux for 5 hours while gradually distilling off methanol formed during the reaction. After cooling, the reaction solution was washed with saturated sodium bicarbonate water, dried over anhydrous sodium sulfate, and concentrated in vacuum. It was further purified by vacuum distillation, obtaining 209 g of a mixture of (1,3-dioxolan-4-yl)methyl 5-norbornene-2-carboxylate and 1,3-dioxan-5-yl 5-norbornene-2-carboxylate (boiling point 111-115° C./530 Pa, yield 93%). was heated under reflux for 5 hours while gradually distilling off methanol formed during the reaction After cooling the reaction solution was washed with saturated sodium bicarbonate water dried over anhydrous sodium sulfate concentrated in vacuum It was further purified by vacuum distillation

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

Procedure: To a mixture of 104 g of glycerol formal, 111 g of triethylamine and 300 ml of toluene, 157 g of 5-norbornene-2-carbonyl chloride was added over one hour at 20° C. After 5 hours of stirring, 200 ml of water was added to stop the reaction and the mixture was allowed to separate. The organic layer was washed with water and saturated sodium chloride water, dried over anhydrous sodium sulfate, and concentrated in vacuum. It was further purified by vacuum distillation, obtaining 213 g of a mixture of (1,3-dioxolan-4-yl)methyl 5-norbornene-2-carboxylate and 1,3-dioxan-5-yl 5-norbornene-2-carboxylate (boiling point 111-115° C./530 Pa, yield 95%). was added over one hour at 20° C the reaction to separate The organic layer was washed with water and saturated sodium chloride water dried over anhydrous sodium sulfate concentrated in vacuum It was further purified by vacuum distillation

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

Procedure: To a mixture of 104 g of glycerol formal, 111 g of triethylamine and 300 ml of toluene, 157 g of 5-norbornene-2-carbonyl chloride was added over one hour at 20° C. After 5 hours of stirring, 200 ml of water was added to stop the reaction and the mixture was allowed to separate. The organic layer was washed with water and saturated sodium chloride water, dried over anhydrous sodium sulfate, and concentrated in vacuum. It was further purified by vacuum distillation, obtaining 213 g of a mixture of (1,3-dioxolan-4-yl)methyl 5-norbornene-2-carboxylate and 1,3-dioxan-5-yl 5-norbornene-2-carboxylate (boiling point 111-115° C./530 Pa, yield 95%). was added over one hour at 20° C the reaction to separate The organic layer was washed with water and saturated sodium chloride water dried over anhydrous sodium sulfate concentrated in vacuum It was further purified by vacuum distillation

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

Procedure: The glycerol formal (Aldrich, 0.26 g, 2.5 mmol), triethylamine (1.1 mL, 8.3 mmol), and methanesulfonyl chloride (0.30 mL, 3.7 mmol) in 20 mL THF were processed as described in Example 1C to give the title compound that was used directly in the next reaction.