反应 #58581

反应方程式

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

收率 166.4%

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

收率 166.4%

溶剂

water

water

water

THF

反应条件

后处理

1. 1
   其他The bulk of tetrahydrofuran was removed under reduced pressure
2. 2
   萃取the resulting mixture (pH 12˜13) was extracted with three 20 mL portion of methylene chloride
3. 3
   其他to remove the oxazolidinone auxiliary
4. 4
   温度The aqueous layer was cooled in an ice bath
5. 5
   萃取The resulting cloudy solution was extracted with five portion of 30 mL ethyl acetate
6. 6
   干燥The combined organic layers are dried over anhydrous magnesium sulfate
7. 7
   过滤filtered
8. 8
   浓缩concentrated under reduced pressure

实验过程

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).

来源