D-Threonine → HCID 86699907, compound

Participants

Reaction Steps

In a round bottom flask NaHCO3 (13.0 g, 155.3 mmol) was suspended in THF (35 mL) and water (70 mL), then D-threonine (7.33 g, 61.6 mmol) and tetrabutylamonium bromide (0.733 g) were added. Amyl chloroformate (10 mL, 68.4 mmol) was added dropwise and the reaction vigorously stirred 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, the collected organic phases were dried over Na2SO4, filtered and the solvent removed under vacuum to yield the tile compound (13.0 g, 90%) as pale yellow oil, which was used in the next step without further purification. Rf=0.26 (Cy/AcOEt 2:8+1% CH3COOH; detection: ninhydrin, bromocresol green). FTIR (cm−1): 3344, 2959, 2932, 2873, 1724, 1529, 1468, 1415 1378, 1258, 1075.

Provenance & Evidence