3-phenylpropyl carbonochloridate

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

Procedure: In a round bottom flask, NaHCO3 (5.94 g, 70.7 mmol) was suspended in THF (15 mL) and water (30 mL), then D-threonine (3.34 g, 28.0 mmol) was added. 3-phenylpropyl chlorocarbonate (6.2 g, 31.2 mmol) was slowly added, followed by a catalytic amount (0.3 g) of tetrabutylamonium bromide. After stirring 18 h at rt., the mixture was diluted with water (100 mL), washed twice with Et2O (2×100 mL) and pH adjusted to 2 with 2M HCl solution. The aqueous phase was extracted with AcOEt (3×150 mL), the collected organic phases were dried over Na2SO4, filtered and the solvent removed under vacuum to give the title compound (1.43 g, 18%), as colorless oil, which was used in the next step without further purification. Rf=0.38 (Cy/AcOEt 2:8+1% CH3COOH). FTIR (cm−1): 3340 (br), 3064, 3030, 2982, 2939, 1730 (br), 1528, 1374, 1241, 1094, 1072, 1048, 781, 749, 703. washed twice with Et2O (2×100 mL) The aqueous phase was extracted with AcOEt (3×150 mL) the collected organic phases were dried over Na2SO4 filtered the solvent removed under vacuum

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

Procedure: In a four necked round bottom flask, triphosgene (5.45 g, 55.1 mmol) was dissolved in toluene (80 mL) under argon. After cooling at 0° C., pyridine (4.8 mL, 58.8 mmol) was added dropwise during 1 h and the resulting suspension stirred for further 1 h at 0° C. 3-phenyl-1-propanol (5 mL, 36.8 mmol) was added dropwise in 30 min. After stirring at rt for 24 h, the solid was filtered off and the solvent removed under vacuum, yielding the title compound (6.2 g, 85%) as pale yellow oil, which was used in the next step without further purification. FTIR (cm−1): 3086, 3065, 3027, 2995, 2932, 2862, 1776, 1743, 1603, 1496, 1454, 1262, 1148, 745, 699. After stirring at rt for 24 h the solid was filtered off 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 (5.94 g, 70.7 mmol) was suspended in THF (15 mL) and water (30 mL), then D-threonine (3.34 g, 28.0 mmol) was added. 3-phenylpropyl chlorocarbonate (6.2 g, 31.2 mmol) was slowly added, followed by a catalytic amount (0.3 g) of tetrabutylamonium bromide. After stirring 18 h at rt., the mixture was diluted with water (100 mL), washed twice with Et2O (2×100 mL) and pH adjusted to 2 with 2M HCl solution. The aqueous phase was extracted with AcOEt (3×150 mL), the collected organic phases were dried over Na2SO4, filtered and the solvent removed under vacuum to give the title compound (1.43 g, 18%), as colorless oil, which was used in the next step without further purification. Rf=0.38 (Cy/AcOEt 2:8+1% CH3COOH). FTIR (cm−1): 3340 (br), 3064, 3030, 2982, 2939, 1730 (br), 1528, 1374, 1241, 1094, 1072, 1048, 781, 749, 703. washed twice with Et2O (2×100 mL) The aqueous phase was extracted with AcOEt (3×150 mL) the collected organic phases were dried over Na2SO4 filtered the solvent removed under vacuum

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

Procedure: In a four necked round bottom flask, triphosgene (5.45 g, 55.1 mmol) was dissolved in toluene (80 mL) under argon. After cooling at 0° C., pyridine (4.8 mL, 58.8 mmol) was added dropwise during 1 h and the resulting suspension stirred for further 1 h at 0° C. 3-phenyl-1-propanol (5 mL, 36.8 mmol) was added dropwise in 30 min. After stirring at rt for 24 h, the solid was filtered off and the solvent removed under vacuum, yielding the title compound (6.2 g, 85%) as pale yellow oil, which was used in the next step without further purification. FTIR (cm−1): 3086, 3065, 3027, 2995, 2932, 2862, 1776, 1743, 1603, 1496, 1454, 1262, 1148, 745, 699. After stirring at rt for 24 h the solid was filtered off the solvent removed under vacuum