5-phenylpentyl carbonochloridate

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

Procedure: In a round bottom flask, NaHCO3 (12.0 g, 143.2 mmol) was suspended in THF (30 mL) and water (60 mL), then D-threonine (6.8 g, 56.8 mmol) was added followed by 5-phenylpentyl chlorocarbonate (14.3 g, 63.1 mmol) and a catalytic amount (0.67 g) of tetrabutylamonium bromide. After stirring 18 h at rt, the mixture was diluted with water, washed twice with Et2O and pH adjusted to 2 with 2M HCl solution. The aqueous phase was extracted with AcOEt (4×150 mL), the collected organic phases were washed with brine, dried over Na2SO4, filtered and the solvent removed under vacuum. The crude was purified by typical silica gel column chromatography, eluting with Cy/AcOEt (20:80+1% CH3COOH), yielding the title compound (3.15 g, 18%), as pale yellow oil. Rf=0.38 (Cy/AcOEt 2:8+1% CH3COOH). FTIR (cm−1): 3332 (br), 3027, 2935, 2859, 1714, 1530, 1454, 1415, 1257, 1072, 1007, 963, 870, 779, 748, 700. 1H NMR (CDCl3): δ 1.26 (d, 3H); 1.39 (m, 2H); 1.62-1.68 (m, 4H); 2.61 (t, 2H); 4.08 (t, 2H); 4.34 (d, 1H); 4.42 (d, 1H); 5.68 (d, 1H); 7.16-7.78 (m, 3H); 7.26-7.28 (m, 2H). washed twice with Et2O The aqueous phase was extracted with AcOEt (4×150 mL) the collected organic phases were washed with brine dried over Na2SO4 filtered the solvent removed under vacuum The crude was purified by typical silica gel column chromatography eluting with Cy/AcOEt (20:80+1% CH3COOH)

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

Procedure: In a round bottom flask, NaHCO3 (12.0 g, 143.2 mmol) was suspended in THF (30 mL) and water (60 mL), then D-threonine (6.8 g, 56.8 mmol) was added followed by 5-phenylpentyl chlorocarbonate (14.3 g, 63.1 mmol) and a catalytic amount (0.67 g) of tetrabutylamonium bromide. After stirring 18 h at rt, the mixture was diluted with water, washed twice with Et2O and pH adjusted to 2 with 2M HCl solution. The aqueous phase was extracted with AcOEt (4×150 mL), the collected organic phases were washed with brine, dried over Na2SO4, filtered and the solvent removed under vacuum. The crude was purified by typical silica gel column chromatography, eluting with Cy/AcOEt (20:80+1% CH3COOH), yielding the title compound (3.15 g, 18%), as pale yellow oil. Rf=0.38 (Cy/AcOEt 2:8+1% CH3COOH). FTIR (cm−1): 3332 (br), 3027, 2935, 2859, 1714, 1530, 1454, 1415, 1257, 1072, 1007, 963, 870, 779, 748, 700. 1H NMR (CDCl3): δ 1.26 (d, 3H); 1.39 (m, 2H); 1.62-1.68 (m, 4H); 2.61 (t, 2H); 4.08 (t, 2H); 4.34 (d, 1H); 4.42 (d, 1H); 5.68 (d, 1H); 7.16-7.78 (m, 3H); 7.26-7.28 (m, 2H). washed twice with Et2O The aqueous phase was extracted with AcOEt (4×150 mL) the collected organic phases were washed with brine dried over Na2SO4 filtered the solvent removed under vacuum The crude was purified by typical silica gel column chromatography eluting with Cy/AcOEt (20:80+1% CH3COOH)

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

Procedure: In a four necked round bottom flask, triphosgene (22.0 g, 74.2 mmol) was dissolved in toluene (325 mL) under argon. After cooling at 0° C., pyridine (19.2 mL, 237.5 mmol) was added dropwise during 1 h and the resulting suspension stirred for 1 h at 0° C. 5-phenylpentanol (25 mL, 148.4 mmol) was added drop wise in 30 min. After stirring at rt for 16 h the solid was filtered-off and the solvent removed under vacuum yielding the title compound (31.7 g, 94%), which was used in the next step without further purification. Rf=0.75 (Cy/AcOEt 8:2). FTIR (cm−1): 3087, 3063, 3027, 2936, 2859, 1778, 1744, 1604, 1496, 1455, 1382, 1260, 1146, 1031, 941, 835, 731, 696. After stirring at rt for 16 h the solid the solvent removed under vacuum

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

Procedure: In a round bottom flask, NaHCO3 (12.0 g, 143.2 mmol) was suspended in THF (30 mL) and water (60 mL), then D-threonine (6.8 g, 56.8 mmol) was added followed by 5-phenylpentyl chlorocarbonate (14.3 g, 63.1 mmol) and a catalytic amount (0.67 g) of tetrabutylamonium bromide. After stirring 18 h at rt, the mixture was diluted with water, washed twice with Et2O and pH adjusted to 2 with 2M HCl solution. The aqueous phase was extracted with AcOEt (4×150 mL), the collected organic phases were washed with brine, dried over Na2SO4, filtered and the solvent removed under vacuum. The crude was purified by typical silica gel column chromatography, eluting with Cy/AcOEt (20:80+1% CH3COOH), yielding the title compound (3.15 g, 18%), as pale yellow oil. Rf=0.38 (Cy/AcOEt 2:8+1% CH3COOH). FTIR (cm−1): 3332 (br), 3027, 2935, 2859, 1714, 1530, 1454, 1415, 1257, 1072, 1007, 963, 870, 779, 748, 700. 1H NMR (CDCl3): δ 1.26 (d, 3H); 1.39 (m, 2H); 1.62-1.68 (m, 4H); 2.61 (t, 2H); 4.08 (t, 2H); 4.34 (d, 1H); 4.42 (d, 1H); 5.68 (d, 1H); 7.16-7.78 (m, 3H); 7.26-7.28 (m, 2H). washed twice with Et2O The aqueous phase was extracted with AcOEt (4×150 mL) the collected organic phases were washed with brine dried over Na2SO4 filtered the solvent removed under vacuum The crude was purified by typical silica gel column chromatography eluting with Cy/AcOEt (20:80+1% CH3COOH)

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

Procedure: In a four necked round bottom flask, triphosgene (22.0 g, 74.2 mmol) was dissolved in toluene (325 mL) under argon. After cooling at 0° C., pyridine (19.2 mL, 237.5 mmol) was added dropwise during 1 h and the resulting suspension stirred for 1 h at 0° C. 5-phenylpentanol (25 mL, 148.4 mmol) was added drop wise in 30 min. After stirring at rt for 16 h the solid was filtered-off and the solvent removed under vacuum yielding the title compound (31.7 g, 94%), which was used in the next step without further purification. Rf=0.75 (Cy/AcOEt 8:2). FTIR (cm−1): 3087, 3063, 3027, 2936, 2859, 1778, 1744, 1604, 1496, 1455, 1382, 1260, 1146, 1031, 941, 835, 731, 696. After stirring at rt for 16 h the solid the solvent removed under vacuum