(2-phenylacetyl) 2-phenylacetate

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

Procedure: A 1.50 M sodium hydroxide solution was added to the hydrochloride salt of (S)-2-amino-2-cyclohexyl-3-butyne 30 (1 equiv). A solution of anhydride (0.17 M, 1 equiv) in chloroform was added to the above solution and heated at reflux for 24 h. The reaction mixture was transferred to a reparatory funnel, and EtOAc (150 mL) and water (15 mL) were added. The organic layer was washed with brine (25 mL), 10 M aqueous sodium hydroxide solution (25 mL×4), brine (25 mL×4), and water (25 mL×2). The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The product was purified by flash chromatography (1:1 hexanes:EtOAc) to afford the desired product. heated at reflux for 24 h The reaction mixture was transferred to a reparatory funnel The organic layer was washed with brine (25 mL), 10 M aqueous sodium hydroxide solution (25 mL×4), brine (25 mL×4), and water (25 mL×2) The organic layer was dried over anhydrous sodium sulfate filtered concentrated under reduced pressure The product was purified by flash chromatography (1:1 hexanes:EtOAc)

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

Procedure: A 1.50 M sodium hydroxide solution was added to the hydrochloride salt of (S)-2-amino-2-cyclohexyl-3-butyne 30 (1 equiv). A solution of anhydride (0.17 M, 1 equiv) in chloroform was added to the above solution and heated at reflux for 24 h. The reaction mixture was transferred to a reparatory funnel, and EtOAc (150 mL) and water (15 mL) were added. The organic layer was washed with brine (25 mL), 10 M aqueous sodium hydroxide solution (25 mL×4), brine (25 mL×4), and water (25 mL×2). The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The product was purified by flash chromatography (1:1 hexanes:EtOAc) to afford the desired product. heated at reflux for 24 h The reaction mixture was transferred to a reparatory funnel The organic layer was washed with brine (25 mL), 10 M aqueous sodium hydroxide solution (25 mL×4), brine (25 mL×4), and water (25 mL×2) The organic layer was dried over anhydrous sodium sulfate filtered concentrated under reduced pressure The product was purified by flash chromatography (1:1 hexanes:EtOAc)

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

Procedure: Phenylacetic acid anhydride (prepared as described in J. Org. Chem., 1588, 30, 1965) (15 g) was added to a suspension of (R)-3-quinuclidinol (5 g) in ethyl acetate (250 ml) at room temperature. After 178 hour the solvent was evaporated and the residue dissolved in hydrochloric acid (2M). This was washed with ethyl acetate, basified with sodium carbonate and extracted with ethyl acetate. The organic extract was dried over sodium sulphate and evaporated to give the title compound as a yellow oil (9 g, 66%). After 178 hour the solvent was evaporated the residue dissolved in hydrochloric acid (2M) This was washed with ethyl acetate extracted with ethyl acetate The organic extract was dried over sodium sulphate evaporated

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

Procedure: Phenylacetic acid anhydride (prepared as described in J. Org. Chem., 1588, 30, 1965) (15 g) was added to a suspension of (R)-3-quinuclidinol (5 g) in ethyl acetate (250 ml) at room temperature. After 178 hour the solvent was evaporated and the residue dissolved in hydrochloric acid (2M). This was washed with ethyl acetate, basified with sodium carbonate and extracted with ethyl acetate. The organic extract was dried over sodium sulphate and evaporated to give the title compound as a yellow oil (9 g, 66%). After 178 hour the solvent was evaporated the residue dissolved in hydrochloric acid (2M) This was washed with ethyl acetate extracted with ethyl acetate The organic extract was dried over sodium sulphate evaporated

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

Procedure: A 1.50 M sodium hydroxide solution was added to the hydrochloride salt of (S)-2-amino-2-cyclohexyl-3-butyne 30 (1 equiv). A solution of anhydride (0.17 M, 1 equiv) in chloroform was added to the above solution and heated at reflux for 24 h. The reaction mixture was transferred to a separatory funnel, and EtOAc (150 mL) and water (15 mL) were added. The organic layer was washed with brine (25 mL), 10 M aqueous sodium hydroxide solution (25 mL×4), brine (25 mL×4), and water (25 mL×2). The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The product was purified by flash chromatography (1:1 hexanes:EtOAc) to afford the desired product. heated at reflux for 24 h The reaction mixture was transferred to a separatory funnel The organic layer was washed with brine (25 mL), 10 M aqueous sodium hydroxide solution (25 mL×4), brine (25 mL×4), and water (25 mL×2) The organic layer was dried over anhydrous sodium sulfate filtered concentrated under reduced pressure The product was purified by flash chromatography (1:1 hexanes:EtOAc)

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

Procedure: In a manner similar to Example 12, a mixture of 8-nitro-1-(hydroxymethyl)-6-(o-chlorophenyl)-4H-s-triazolo[4,3-a][1,4]benzodiazepine and phenylacetic anhydride was heated on the water bath to give 8-nitro-1-(hydroxymethyl)-6-(o-chlorophenyl)-4H-s-triazolo[4,3-a][1,4]benzodiazepine phenylacetate (ester).

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

Procedure: A 1.50 M sodium hydroxide solution was added to the hydrochloride salt of (S)-2-amino-2-cyclohexyl-3-butyne 30 (1 equiv). A solution of anhydride (0.17 M, 1 equiv) in chloroform was added to the above solution and heated at reflux for 24 h. The reaction mixture was transferred to a reparatory funnel, and EtOAc (150 mL) and water (15 mL) were added. The organic layer was washed with brine (25 mL), 10 M aqueous sodium hydroxide solution (25 mL×4), brine (25 mL×4), and water (25 mL×2). The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The product was purified by flash chromatography (1:1 hexanes:EtOAc) to afford the desired product. heated at reflux for 24 h The reaction mixture was transferred to a reparatory funnel The organic layer was washed with brine (25 mL), 10 M aqueous sodium hydroxide solution (25 mL×4), brine (25 mL×4), and water (25 mL×2) The organic layer was dried over anhydrous sodium sulfate filtered concentrated under reduced pressure The product was purified by flash chromatography (1:1 hexanes:EtOAc)

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

Procedure: Phenylacetic acid anhydride (prepared as described in J. Org. Chem., 1588, 30, 1965) (15 g) was added to a suspension of (R)-3-quinuclidinol (5 g) in ethyl acetate (250 ml) at room temperature. After 178 hour the solvent was evaporated and the residue dissolved in hydrochloric acid (2M). This was washed with ethyl acetate, basified with sodium carbonate and extracted with ethyl acetate. The organic extract was dried over sodium sulphate and evaporated to give the title compound as a yellow oil (9 g, 66%). After 178 hour the solvent was evaporated the residue dissolved in hydrochloric acid (2M) This was washed with ethyl acetate extracted with ethyl acetate The organic extract was dried over sodium sulphate evaporated