Reacción #58581

Ecuación de reacción

sodium sulfite

hydrogen peroxide

Acyloxazolidinone

3-(2(R)-cyclopentylmethyl-3(S)-hydroxyl-5-phenyl-1-oxopentyl)-4(R)-(phenylmethyl)-2-oxazolidinone

lithium hydroxide

→

desired acid 4

Rendimiento 166.4%

2(R)-cyclopentylmethyl-3 (S)-hydroxyl-5-phenylpentanoic acid

Rendimiento 166.4%

Disolventes

water

water

water

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe bulk of tetrahydrofuran was removed under reduced pressure
2. 2
   Extracciónthe resulting mixture (pH 12˜13) was extracted with three 20 mL portion of methylene chloride
3. 3
   Otroto remove the oxazolidinone auxiliary
4. 4
   TemperaturaThe aqueous layer was cooled in an ice bath
5. 5
   ExtracciónThe resulting cloudy solution was extracted with five portion of 30 mL ethyl acetate
6. 6
   SecadoThe combined organic layers are dried over anhydrous magnesium sulfate
7. 7
   Filtraciónfiltered
8. 8
   Concentraciónconcentrated under reduced pressure

Procedimiento

Acyloxazolidinone 3 (226 mg, 0.500 mmol) was dissolved in 3 mL of THF and 1 mL of distilled water. The resulting solution was cooled to 0° C. To this solution was added 30% aqueous hydrogen peroxide (0.40 mL, 4.0 mmol), followed by a solution of lithium hydroxide (19 mg, 0.80 mmol) in 0.5 mL of distilled water. After the solution was stirred for 16 h, sodium sulfite (567 mg, 4.50 mmol) in 3 mL of distilled water was added. The bulk of tetrahydrofuran was removed under reduced pressure, and the resulting mixture (pH 12˜13) was extracted with three 20 mL portion of methylene chloride to remove the oxazolidinone auxiliary. The aqueous layer was cooled in an ice bath and acidified to pH 1 with 6 M aqueous hydrochloric acid. The resulting cloudy solution was extracted with five portion of 30 mL ethyl acetate. The combined organic layers are dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to yield 230 mg (81%) of the desired acid 4 as a white solid. 1H NMR (300 MHz, CDCl3) δ 7.18-7.35 (5 H, m), 3.87 (1 H, m), 2.81-2.87 (1 H, m), 2.60-2.76 (1 H, m); 2.54-2.60 (1 H, m), 1.00-1.95 (m, 13 H).

Fuente