反应详情

A solution of the ester 21g (0.775 g, 1.39 mmol) in 1:1:1 THF-Methanol-aq. 1M LiOH (36 ml) was stirred at rt for 3.5 h after which TLC (95:5 and 9:1 dichloromethane-methanol) and LC-MS indicated complete conversion into the carboxylic acid. The reaction mixture was then concentrated into approximately ⅓ of the volume, then diluted with water (10 ml) and acidified to approx. pH 4 using aq. 10% citric acid (60 ml) upon which a precipitate formed. The mixture was washed with ethyl acetate (3×25 ml) and the combined organic layers were washed with brine (2×50 ml), then dried (Na2SO4), filtered and concentrated. The residue was concentrated from toluene (3×10 ml) which gave the crude title compound as an off-white foam (0.75 g, quantitative). LR-MS: Calcd for C28H40N3O7: 530. Found: 530 [M−H].

1. concentrationThe reaction mixture was then concentrated into approximately ⅓ of the volume
2. additiondiluted with water (10 ml)
3. customformed
4. washThe mixture was washed with ethyl acetate (3×25 ml)
5. washthe combined organic layers were washed with brine (2×50 ml)
6. dry with materialdried (Na2SO4)
7. filtrationfiltered
8. concentrationconcentrated
9. concentrationThe residue was concentrated from toluene (3×10 ml) which