methyl (2S)-2-amino-4-methylsulfanylbutanoate

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

Procedure: The resultant product from Example 16C is coupled to methionine methyl ester according to the procedure of Example 1C to give the title compound.

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

Procedure: The resultant product from Example 14B is coupled to methionine methyl ester according to the procedure of Example 1C to give the title compound.

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

Procedure: A solution of the resultant thiophenol from Example 12A (1.0 equivalent) is treated with 2-bromopyridine hydrobromide (1.0 equivalent) in the presence of a NaH (2.0 equivalents), or K2CO3 (3.0 equivalents) in DMF or pyridine. The product is isolated by removal of the solvent and chromatography on silica gel. The resultant ester is hydrolyzed according to the procedure of Example 6C and then is coupled to methionine methyl ester according to the procedure of Example 1C to give the title compound. The product is isolated by removal of the solvent and chromatography on silica gel

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

Procedure: The resultant product from Example 13B is coupled to methionine methyl ester according to the procedure of Example 1C to give the title compound.

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

Procedure: The resultant product from Example 6C is coupled to methionine methyl ester according to the procedure of Example 1C to give the title compound.

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

Procedure: The resultant product from Example 16C is coupled to methionine methyl ester according to the procedure of Example 1C to give the title compound.

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

Procedure: A solution of the resultant thiophenol from Example 12A (1.0 equivalent) is treated with 2-bromopyridine hydrobromide (1.0 equivalent) in the presence of a NaH (2.0 equivalents), or K2CO3 (3.0 equivalents) in DMF or pyridine. The product is isolated by removal of the solvent and chromatography on silica gel. The resultant ester is hydrolyzed according to the procedure of Example 6C and then is coupled to methionine methyl ester according to the procedure of Example 1C to give the title compound. The product is isolated by removal of the solvent and chromatography on silica gel

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

Procedure: The resultant product from Example 13B is coupled to methionine methyl ester according to the procedure of Example 1C to give the title compound.

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

Procedure: The resultant product from Example 6C is coupled to methionine methyl ester according to the procedure of Example 1C to give the title compound.

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: At about 0° C., acetyl chloride (15 mL) was added dropwise to methanol (100 mL). After stirring for about 10 minutes at about 0° C., L-methionine (8.5 g, 57 mmol) was added and the resulting solution was stirred for about 10 minutes. The solution was then heated at reflux for about 4 hours, and then maintained at ambient temperature for about 16 hours. The solvent was removed in vacuo, the resulting residue was dissolved in chloroform (100 mL), and the solution was neutralized to pH 7-8 by the careful addition of a saturated aqueous sodium bicarbonate solution. Following standard extractive workup with chloroform, the resulting residue was kept under high vacuum for about two hours to afford the title product as a colourless oily liquid, which was used directly in the next step without any further purification (crude yield 6 g, 65%). the resulting solution was stirred for about 10 minutes The solution was then heated at reflux for about 4 hours maintained at ambient temperature for about 16 hours The solvent was removed in vacuo the resulting residue was dissolved in chloroform (100 mL) the solution was neutralized to pH 7-8 by the careful addition of a saturated aqueous sodium bicarbonate solution the resulting residue was kept under high vacuum for about two hours

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

Procedure: The resultant product from Example 16C is coupled to methionine methyl ester according to the procedure of Example 1C to give the title compound.

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

Procedure: The resultant product from Example 14B is coupled to methionine methyl ester according to the procedure of Example 1C to give the title compound.