反応 #5498

反応方程式

N-[[trans 3-(acetylthiomethyl)-2-oxo-1-azacyclodecan-10-yl]-carbonyl]-(R)-4-benzyl-2-oxazolidinone

Lithium hydroxide hydrate

→

trans 3-(acetylthiomethyl)-2-oxo-1-azacyclodecane-10-carboxylic acid

溶媒

water

tetrahydrofuran

反応条件

後処理

1. 1
   その他The solvent is then evaporated
2. 2
   その他the residue is partitioned between saturated sodium bicarbonate and methylene chloride
3. 3
   抽出The aqueous layer is extracted several times with methylene chloride
4. 4
   抽出The aqueous layer is extracted several times with ethyl acetate
5. 5
   乾燥the combined organic layers dried (MgSO4)
6. 6
   その他the solvent is evaporated

実験手順

The more polar major chiral isomer of N-[[trans 3-(acetylthiomethyl)-2-oxo-1-azacyclodecan-10-yl]-carbonyl]-(R)-4-benzyl-2-oxazolidinone (1.23 g, 2.75 mmol) is dissolved in tetrahydrofuran (45.0 mL) and water (15.0 mL), and the reaction is cooled to 0° C. Lithium hydroxide hydrate (0.116 g, 2.75 mmol) is added, and the reaction is stirred at 0° C. for 45 minutes. The solvent is then evaporated, and the residue is partitioned between saturated sodium bicarbonate and methylene chloride. The aqueous layer is extracted several times with methylene chloride, and then the aqueous layer is acidified with 2.5N hydrochloric acid to pH=3. The aqueous layer is extracted several times with ethyl acetate, the combined organic layers dried (MgSO4) and the solvent is evaporated, to give one enantiomer of trans 3-(acetylthiomethyl)-2-oxo-1-azacyclodecane-10-carboxylic acid, m.p. 144°-145° C.; [α]D +88.36° (c=6.9 mg/ml, CH2Cl2), which is assigned the 3R, 10S configuration.

出典