(S)-(-)-1,1,2-Triphenylethane-1,2-diol

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

Procedure: To aqueous sodium hydroxide (2.03 ml, 1.5 M, 3.04 mmol) at ambient temperature was added omeprazole (1 g, 2.90 mmol) in 5 portions over 10 min. On complete dissolution, ethanol (35 ml) and (S)-1,1,2-triphenyl-1,2-ethanediol (1.26 g, 4.34 mmol) were added. To the resulting colourless solution at ambient temperature was added a solution of aqueous acetic acid (3.04 ml, 1 M, 3.04 mmol) dropwise over 1 h and, on complete addition, stirring was continued for 4 h. The solid was filtered, was washed with ethanol (3×15 ml) and was dried in vacuo to afford (S)-omeprazole.2[(S)-1,1,2-triphenyl-1,2-ethanediol] (925 mg, 69%, 96.4% ee) as a white powder. were added on complete addition The solid was filtered was washed with ethanol (3×15 ml) was dried in vacuo

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

Procedure: A suspension of omeprazole (250 mg, 0.72 mmol) and (S)-1,1,2-triphenyl-1,2-ethanediol (315 mg, 1.09 mmol) in toluene (8.8 ml) at ambient temperature was stirred for 18 h. The solid was filtered, was washed with toluene (2×2 ml) and was dried in vacuo to afford (S)-omeprazole.2[(S)-1,1,2-triphenyl-1,2-ethanediol] (320 mg, 96%, 94.6% e.e.) as a white powder. The solid was filtered was washed with toluene (2×2 ml) was dried in vacuo

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

Procedure: A suspension of omeprazole (250 mg, 0.72 mmol) and (S)-1,1,2-triphenyl-1,2-ethanediol (315 mg, 1.09 mmol) in methyl isobutyl ketone (8.8 ml) at ambient temperature was stirred for 72 h. The solid was filtered, was washed with methyl isobutyl ketone (2×2 ml) and was dried in vacuo to afford (S)-omeprazole.2[(S)-1,1,2-triphenyl-1,2-ethanediol] (286 mg, 69.1% e.e.) as a white powder. The solid was filtered was washed with methyl isobutyl ketone (2×2 ml) was dried in vacuo

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

Procedure: A suspension of omeprazole (250 mg, 0.72 mmol) and (S)-1,1,2-triphenyl-1,2-ethanediol (315 mg, 1.09 mmol) in anisole (8.8 ml) at ambient temperature was stirred for 72 h. The solid was filtered, was washed with anisole (2×2 ml) and was dried in vacuo to afford (S)-omeprazole.2[(S)-1,1,2-triphenyl-1,2-ethanediol] (265 mg, 79%, 96.6% e.e.) as a white powder. The solid was filtered was washed with anisole (2×2 ml) was dried in vacuo

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

Procedure: A suspension of omeprazole (20 g, 57.9 mmol) and (S)-1,1,2-triphenyl-1,2-ethanediol (25.2 g, 86.9 mmol) in ethanol (700 ml) at ambient temperature was stirred for 30 h. The solid was filtered, was washed with ethanol (2×150 ml) and was dried in vacuo to afford (S)-omeprazole.2[(S)-1,1,2-triphenyl-1,2-ethanediol] (24.1 g, 90%, 95.5% e.e.) as a white powder. The solid was filtered was washed with ethanol (2×150 ml) was dried in vacuo

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

Procedure: A mixture of omeprazole (500 mg, 1.45 mmol) and (S)-1,1,2-triphenyl-1,2-ethanediol (630 mg, 2.17 mmol, 99.3% e.e. recovered according to Example 24) was dissolved in a minimum volume of toluene (18 ml) at 90° C. On dissolution, the solution was cooled to ambient temperature slowly with vigorous stirring, and on reaching this temperature was stirred for a further 1 h. The precipitate was filtered, was washed with toluene (2×5 ml) and was dried in vacuo to afford (S)-omeprazole.2[(S)-1,1,2-triphenyl-1,2-ethanediol] inclusion complex (627 mg, 94%, 93.7% e.e.) as an off-white powder. On dissolution The precipitate was filtered was washed with toluene (2×5 ml) was dried in vacuo

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

Procedure: A mixture of omeprazole (250 mg, 0.72 mmol) and (S)-1,1,2-triphenyl-1,2-ethanediol (315 mg, 1.08 mmol) was dissolved in a minimum volume of chloroform (4 ml) at reflux temperature. On dissolution, the solution was cooled to ambient temperature slowly with vigorous stirring, and on reaching this temperature was stirred for a further 1 h. The precipitate was filtered, was washed with chloroform (2×2 ml) and was dried in vacuo to afford (S)-omeprazole.2[(S)-1,1,2-triphenyl-1,2-ethanediol] inclusion complex (141 mg, 42%, 94% e.e.) as an off-white powder. at reflux temperature On dissolution The precipitate was filtered was washed with chloroform (2×2 ml) was dried in vacuo

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

Procedure: A mixture of omeprazole (250 mg, 0.72 mmol) and (S)-1,1,2-triphenyl-1,2-ethanediol (315 mg, 1.08 mmol) was dissolved in a minimum volume of acetonitrile (4 ml) at reflux temperature. On dissolution, the solution was cooled to ambient temperature slowly with vigorous stirring, and on reaching this temperature was stirred for a further 1 h. The precipitate was filtered, was washed with acetonitrile (2×2 ml) and was dried in vacuo to afford (S)-omeprazole.2[(S)-1,1,2-triphenyl-1,2-ethanediol] inclusion complex (239 mg, 71%, 95% e.e.) as an off-white powder. at reflux temperature On dissolution The precipitate was filtered was washed with acetonitrile (2×2 ml) was dried in vacuo

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

Procedure: A mixture of omeprazole (250 mg, 0.72 mmol) and (S)-1,1,2-triphenyl-1,2-ethanediol (315 mg, 1.08 mmol) was dissolved in a minimum volume of anisole (4 ml) at 90° C. On dissolution, the solution was cooled to ambient temperature slowly with vigorous stirring, and on reaching this temperature was stirred for a further 1 h. The precipitate was filtered, was washed with anisole (2×2 ml) and was dried in vacuo to afford (S)-omeprazole.2[(S)-1,1,2-triphenyl-1,2-ethanediol] inclusion complex (215 mg, 64%, 96% e.e.) as an off-white powder. On dissolution The precipitate was filtered was washed with anisole (2×2 ml) was dried in vacuo

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

Procedure: A mixture of omeprazole (250 mg, 0.72 mmol) and (S)-1,1,2-triphenyl-1,2-ethanediol (315 mg, 1.08 mmol) was dissolved in a minimum volume of methyl isobutyl ketone (8 ml) at 90° C. On dissolution, the solution was cooled to ambient temperature slowly with vigorous stirring, and on reaching this temperature was stirred for a further 1 h. The precipitate was filtered, was washed with methyl isobutyl ketone (2×2 ml) and was dried in vacuo to afford (S)-omeprazole.2[(S)-1,1,2-triphenyl-1,2-ethanediol] inclusion complex (253 mg, 76%, 94% e.e.) as an off-white powder. On dissolution The precipitate was filtered was washed with methyl isobutyl ketone (2×2 ml) was dried in vacuo

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

Procedure: A mixture of omeprazole (250 mg, 0.72 mmol) and (S)-1,1,2-triphenyl-1,2-ethanediol (315 mg, 1.08 mmol) was dissolved in a minimum volume of isopropyl alcohol (10 ml) at reflux temperature. On dissolution, the solution was cooled to ambient temperature slowly with vigorous stirring, and on reaching this temperature was stirred for a further 1 h. The precipitate was filtered, was washed with isopropyl alcohol (2×2 ml) and was dried in vacuo to afford (S)-omeprazole.2[(S)-1,1,2-triphenyl-1,2-ethanediol] inclusion complex (240 mg, 72%, 97% e.e.) as an off-white powder. at reflux temperature On dissolution The precipitate was filtered was washed with isopropyl alcohol (2×2 ml) was dried in vacuo

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

Procedure: A mixture of omeprazole (250 mg, 0.72 mmol) and (S)-1,1,2-triphenyl-1,2-ethanediol (315 mg, 1.08 mmol) was dissolved in a minimum volume of toluene (11 ml) at 90° C. On dissolution, the solution was cooled to ambient temperature slowly with vigorous stirring, and on reaching this temperature was stirred for a further 1 h. The precipitate was filtered, was washed with toluene (2×3 ml) and was dried in vacuo to afford (S)-omeprazole.2[(S)-1,1,2-triphenyl-1,2-ethanediol] inclusion complex (291 mg, 87%, 95% e.e.) as an off-white powder. On dissolution The precipitate was filtered was washed with toluene (2×3 ml) was dried in vacuo