Sodium Sulfite → (2R)-5-Phenyl-2-methylpentanoic acid

Temperature

0 °C

(4S)-3-((2R)-5-Phenyl-2-methyl-1 -oxopentyl)-4-isopropyl-1,3-oxazolidin -2-one (0.25 g, 0.83 mmol), prepared by the method described in J. Org. Chem. 59: 2261, (1994), was dissolved in 4.2 mL of 4:1 THF:H2O, cooled to 0° C. and purged with N2. 30% Hydrogen peroxide (0.34 mL) was added dropwise, followed by a dropwise addition of a solution of LiOH·H2O (31.9 mg, 1.3 mmol) and 1.7 mL H2O. The reaction mixture was stirred at 0° C. for 1 hour, then a solution of sodium sulfite (0.42 g, 3.3 mmol) in 2.5 mL of H2O was added. THF was evaporated in vacuo, and H2O was added to the residue. This mixture was washed with CH2Cl2 (3×). The aqueous layer was cooled to 0° C., acidified with aqueous hydrochloric acid and extracted (5×) with EtOAc. The combined EtOAc extracts were dried (MgSO4), filtered, and concentrated in vacuo to afford the title compound (0.11 g) as a colorless oil. 1HNMR (300 MHz, CDCl3) δ 1.18 (d, 3H), 1.50 (m, 3H), 1.60-1.80 (m, 3H), 2.5 (m, 1H), 2.62 (t, 2H), 7.08 (m, 3H), 7.29 (m, 2H). MS (DCl/NH3) m/e 210 (M+NH4)+.

1. custompurged with N2
2. addition30% Hydrogen peroxide (0.34 mL) was added dropwise
3. customTHF was evaporated in vacuo, and H2O
4. additionwas added to the residue
5. washThis mixture was washed with CH2Cl2 (3×)
6. temperatureThe aqueous layer was cooled to 0° C.
7. extractionextracted (5×) with EtOAc
8. dry with materialThe combined EtOAc extracts were dried (MgSO4)
9. filtrationfiltered
10. concentrationconcentrated in vacuo

ORD record

ord-c41fabd17d2d4faaae41576009c8479f

Source dataset

uspto-grants-1997_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05631401