2-Phenylpropionic acid → HCID 68871308, compound

Lithium bis(trimethylsilyl)amide (3.23 g, 19.3 mmol) was added to 8 mL of tetrahydrofuran and the resulting solution was cooled in an ice bath. Addition of a solution of 2-phenyl-propionic acid (1.16 g, 7.73 mmol) in 1 mL of tetrahydrofuran to the reaction solution was followed by addition of (S)-1-bromo-3-methyl-pentane (2.05 g, 12.4 mmol). The reaction vessel was removed from the cooling bath, placed in a 50° C. oil bath, and the reaction solution was stirred for 17 hours. After concentration, the resulting residue was dissolved in 25 mL of 1 N NaOH, washed with 25 mL of 2:1 hexane/iso-propyl acetate, acidified to pH 1 with 6 N HCl, and extracted with ethyl acetate (3× 30 mL). The combined organic layers were dried over Na2SO4 and concentrated to give 1.63 g (90%) of a clear oil. 1H NMR (300 MHz, CDCl3): δ ppm 0.83 (m, 6H) 1.20 (m, 5H) 1.57 (s, 3H) 1.98 (m, 2H) 7.35 (m, 5H).

1. temperaturethe resulting solution was cooled in an ice bath
2. customThe reaction vessel was removed from the cooling bath
3. customplaced in a 50° C.
4. concentrationAfter concentration
5. dissolutionthe resulting residue was dissolved in 25 mL of 1 N NaOH
6. washwashed with 25 mL of 2:1 hexane/iso-propyl acetate
7. extractionextracted with ethyl acetate (3× 30 mL)
8. dry with materialThe combined organic layers were dried over Na2SO4
9. concentrationconcentrated

ORD record

ord-b8ab2cc7a00e42ea9935d6b2751c24d6

Source dataset

uspto-grants-2009_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07538105B2