反应详情

温度

0 °C

To a solution of (S)-methyl 2-(tert-butoxycarbonyl)-3-(2,2-dimethylbenzo[d][1,3]dioxol-5-yl)propanoate (5000 mg, 14229 μmol) in 100 mL of THF at 0° C. was added lithium hydroxide (0.2 M, 28458 μl, 14229 μmol) over 10 minutes. After stirring at 0° C. for 1 hour the reaction was poured into a separatory funnel and 100 mL of water was added. The mixture was washed with 150 mL of ether, then acidified to pH 2-3- with 1 N HCl. Ethyl acetate was added, the layers were separated and the aqueous layer was extracted with ethyl acetate (3×100 mL). The combined organics were washed with water and then brine before being dried over sodium sulfate, filtered and concentrated to furnish (S)-2-(tert-butoxycarbonyl)-3-(2,2-dimethylbenzo[d][1,3]dioxol-5-yl)propanoic acid (4005 mg, 83% yield) as a colorless viscous oil.

1. additionwas poured into a separatory funnel
2. washThe mixture was washed with 150 mL of ether
3. additionEthyl acetate was added
4. customthe layers were separated
5. extractionthe aqueous layer was extracted with ethyl acetate (3×100 mL)
6. washThe combined organics were washed with water
7. dry with materialbrine before being dried over sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated