반응 #58581

반응 방정식

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

수율 166.4%

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

수율 166.4%

용매

water

water

water

THF

반응 조건

후처리

1. 1
   기타The bulk of tetrahydrofuran was removed under reduced pressure
2. 2
   추출the resulting mixture (pH 12˜13) was extracted with three 20 mL portion of methylene chloride
3. 3
   기타to remove the oxazolidinone auxiliary
4. 4
   온도The aqueous layer was cooled in an ice bath
5. 5
   추출The resulting cloudy solution was extracted with five portion of 30 mL ethyl acetate
6. 6
   건조The combined organic layers are dried over anhydrous magnesium sulfate
7. 7
   여과filtered
8. 8
   농축concentrated under reduced pressure

실험 절차

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).

출처