Hydrochloric Acid → HCID 44223289, compound

Temperature

90 °C

The crude (S)-benzyl 2-(dibenzylamino)pentanoate (3) (2.2 Kg) was dissolved in methanol (5.5 L). A previously prepared, cold (0-5° C.) solution of sodium hydroxide (568 g; 14.2 mol) in water (6 L) was added to the solution of (3), and the resulting mixture heated at 90° C. for 20 hours. The reaction mixture was then allowed to cool to ambient temperature, and the methanol evaporated under reduced pressure. The residue was diluted with water (25 L), and extracted with methyl t-butyl ether/hexane (1:1; 2×5 L) to remove the benzyl alcohol formed in the hydrolysis. The basic aqueous layer was acidified to pH 2 with 6M aqueous hydrochloric acid (4 L), then extracted with ethyl acetate (2×8 L). The combined organic extracts were dried over sodium sulfate and the solvent removed under reduced pressure, to afford a semi solid, which was washed with hexanes (8 L) to provide 1.12 Kg of (S)-2-(dibenzylamino)pentanoic acid, a compound of formula (4), as a white solid.

1. customA previously prepared
2. temperatureto cool to ambient temperature
3. customthe methanol evaporated under reduced pressure
4. additionThe residue was diluted with water (25 L)
5. extractionextracted with methyl t-butyl ether/hexane (1:1; 2×5 L)
6. customto remove the benzyl alcohol
7. customformed in the hydrolysis
8. extractionextracted with ethyl acetate (2×8 L)
9. dry with materialThe combined organic extracts were dried over sodium sulfate
10. customthe solvent removed under reduced pressure
11. customto afford a semi solid, which
12. washwas washed with hexanes (8 L)

ORD record

ord-2e40e8e323804acdaafd9e4de1c2ac90

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08431733B2