Acetone → HCID 13778607, compound

A mixture of L-valine (29.29 g, 250 mmol)6 and acetone (18.36 mL, 500 mmol, Malinckrodt Baker Inc., Paris, Ky. 40361) was agitated in an atmosphere of hydrogen (pressure, 41-50 psi) at room temperature in 500 mL ethanol in the presence of Pd/C (20%, 4 g) until the absorption of hydrogen had ceased. The mixture was filtered, and the filter cake washed with 450 mL 1 M HCl. The filtrate was treated with concentrated aqueous sodium hydroxide (29.8%) to adjust the pH to 5.5, and concentrated to dryness under reduced pressure. The white solid thus obtained was extracted by stirring 2 to 3 hours vigorously with 250 mL methanol followed by filtration. This process was repeated several times. The combined extracts were concentrated under reduced pressure, and the white solid thus obtained was recrystallized from methanol and dried under vacuum to give 36.48 g (92%) of the pure titled compound in two crops as a white solid: mp >300° C. APCI-MS m/z 160.2 (MH+).

1. filtrationThe mixture was filtered
2. washthe filter cake washed with 450 mL 1 M HCl
3. additionThe filtrate was treated with concentrated aqueous sodium hydroxide (29.8%)
4. concentrationconcentrated to dryness under reduced pressure
5. customThe white solid thus obtained
6. extractionwas extracted
7. filtrationfollowed by filtration
8. concentrationThe combined extracts were concentrated under reduced pressure
9. customthe white solid thus obtained
10. customwas recrystallized from methanol
11. customdried under vacuum

ORD record

ord-1a4b7d71c99d4d6599356b5ce76ec737

Source dataset

uspto-grants-2002_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06458781B1