Benzyl chloroformate → HCID 68719246, compound

To a mixture of ((R)-3-amino-2-hydroxy-propyl)-cyclohexylmethyl-phosphinic acid (7.05 g, 30 mmol) and potassium carbonate (12.42 g, 90 mmol) in water (90 mL) and THF (30 mL) was added benzyl chloroformate (7.65 g, 45 mmol). After stirring for 3 h at room temperature, the reaction mixture was diluted with ethyl acetate (150 mL) and 2N HCl (90 mL). After stirring vigorously for 10 min the aqueous layer was removed and the organic layer was diluted with heptane (200 mL). The resulting white precipitate was collected to yield ((R)-3-benzyloxycarbonylamino-2-hydroxy-propyl)-cyclohexylmethyl-phosphinic acid (10.5 g, 28 mmol). 1H NMR (CDCl3, 300 MHz): δ 7.32 (m, 5H), 5.45 (br s, 1H), 5.10 (s, 2H), 4.2 (m, 1H), 3.4 (dd, 1H), 3.20 (dd, 1H), 2.01-1.55 (m, 10H), 1.40-0.95 (m, 5H). 31P NMR (CDCl3, 300 MHz): δ 57.3. LC/MS m/z: [M+H]+=370.

1. stirringAfter stirring vigorously for 10 min the aqueous layer
2. customwas removed
3. additionthe organic layer was diluted with heptane (200 mL)
4. customThe resulting white precipitate was collected

ORD record

ord-bbdb7b81cb6b41e896824edb573535bc

Source dataset

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07687540B2