bis(methylsulfanyl)methanone

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: S,S-dimethyl carbonodithioate (1.467 g, 12.00 mmol) was added with vigorous stirring to a solution of (E)-pent-2-enoic acid (2.002 g, 20 mmol) in 30% KOH solution (prepared from potassium hydroxide (3.87 g, 69 mmol) and Water (10 mL)). The reaction mixture was slowly heated to 90° C. over a period of 20-30 min Heating was continued for 3 hours before the reaction was cooled down to 25° C. and quenched slowly with HCl. The mixture was then extracted with DCM (3×30 mL), combined organic layer dried and concentrated to give 3-(methylthio)pentanoic acid (2.7 g, 18.22 mmol, 91% yield) as light orange oil: IR (Thin film) 2975, 1701 cm−1; 1H NMR (400 MHz, CDCl3) δ 2.92 (qd, J=7.3, 5.6 Hz, 1H), 2.63 (d, J=7.2 Hz, 2H), 2.08 (s, 3H), 1.75-1.51 (m, 2H), 1.03 (t, J=7.4 Hz, 3H); 13C NMR (101 MHz, CDCl3) δ 178.14, 43.95, 39.78, 27.04, 12.95, 11.29; EIMS m/z 148. Heating was cooled down to 25° C. quenched slowly with HCl The mixture was then extracted with DCM (3×30 mL) dried concentrated

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-triisopropylsilanyloxy-propane-1,3-diamine (Step P10) (27.8 g, 113 mmol) in MeOH (450 mL) was added S,S-dimethyl carbonodithioate (17.7 mL, 169 mmol) and the mixture was stirred at 60° C. for 20 h. The reaction mixture was concentrated. The residue was purified by flash chromatography(CH2Cl2/MeOH, 100:0→5:1) to afford the title compound. ESI-MS: [M+H]+273.3 (LC-MS 1-flow injection). The reaction mixture was concentrated The residue was purified by flash chromatography(CH2Cl2/MeOH, 100:0→5:1)

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-triisopropylsilanyloxy-propane-1,3-diamine (Step P10) (27.8 g, 113 mmol) in MeOH (450 mL) was added S,S-dimethyl carbonodithioate (17.7 mL, 169 mmol) and the mixture was stirred at 60° C. for 20 h. The reaction mixture was concentrated. The residue was purified by flash chromatography(CH2Cl2/MeOH, 100:0→5:1) to afford the title compound. ESI-MS: [M+H]+273.3 (LC-MS 1-flow injection). The reaction mixture was concentrated The residue was purified by flash chromatography(CH2Cl2/MeOH, 100:0→5:1)

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: S,S-dimethyl carbonodithioate (1.467 g, 12.00 mmol) was added with vigorous stirring to a solution of (E)-pent-2-enoic acid (2.002 g, 20 mmol) in 30% KOH solution (prepared from potassium hydroxide (3.87 g, 69 mmol) and Water (10 mL)). The reaction mixture was slowly heated to 90° C. over a period of 20-30 min. Heating was continued for 3 hours before the reaction was cooled down to 25° C. and quenched slowly with HCl. The mixture was then extracted with DCM (3×30 mL), combined organic layer dried and concentrated to give 3-(methylthio)pentanoic acid (2.7 g, 18.22 mmol, 91% yield) as light orange oil: IR (Thin film) 2975, 1701 cm−1; 1H NMR (400 MHz, CDCl3) δ 2.92 (qd, J=7.3, 5.6 Hz, 1H), 2.63 (d, J=7.2 Hz, 2H), 2.08 (s, 3H), 1.75-1.51 (m, 2H), 1.03 (t, J=7.4 Hz, 3H); 13C NMR (101 MHz, CDCl3) δ 178.14, 43.95, 39.78, 27.04, 12.95, 11.29; EIMS m/z 148. Heating was cooled down to 25° C. quenched slowly with HCl The mixture was then extracted with DCM (3×30 mL) dried concentrated

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: S,S-dimethyl carbonodithioate (1.467 g, 12.00 mmol) was added with vigorous stirring to a solution of (E)-pent-2-enoic acid (2.002 g, 20 mmol) in 30% KOH solution (prepared from potassium hydroxide (3.87 g, 69 mmol) and Water (10 mL)). The reaction mixture was slowly heated to 90° C. over a period of 20-30 min Heating was continued for 3 hours before the reaction was cooled down to 25° C. and quenched slowly with HCl. The mixture was then extracted with DCM (3×30 mL), combined organic layer dried and concentrated to give 3-(methylthio)pentanoic acid (2.7 g, 18.22 mmol, 91% yield) as light orange oil: IR (Thin film) 2975, 1701 cm−1; 1H NMR (400 MHz, CDCl3) δ 2.92 (qd, J=7.3, 5.6 Hz, 1H), 2.63 (d, J=7.2 Hz, 2H), 2.08 (s, 3H), 1.75-1.51 (m, 2H), 1.03 (t, J=7.4 Hz, 3H); 13C NMR (101 MHz, CDCl3) δ 178.14, 43.95, 39.78, 27.04, 12.95, 11.29; EIMS m/z 148. Heating was cooled down to 25° C. quenched slowly with HCl The mixture was then extracted with DCM (3×30 mL) dried concentrated