反应详情

To a solution of (S)-4-((S)-2-Amino-propyl)-6,6-dimethyl-morpholine-3 carboxylic acid (6-chloro-9H-beta-carbolin-8-yl)-amide hydrochloride salt (3.45 g, 6.59 mmole) in 68 ml of dry pyridine, was added in three portions over 1.5 hr, a 3M DCM solution of methyl chloroformate (9.2 ml, 27.6 mmole, 4.2 eq). After 2 h, 10 ml of water were added and the mixture was concentrated to dryness. The residue was partitioned into 150 ml Of EtOAc and 100 ml of an aqueous 0.5M solution of K2CO3. The separated aqueous phase was extracted with 50 ml of EtOAc. The combined organic extracts were successively washed with water (2×50 ml) and brine (50 ml), dried over Na2SO4 and concentrated to dryness. The residue was purified on silica (5% MeOH/CH2Cl2) to give 2.48 g(thick oil, 77% yield) of the desired product.

1. concentrationthe mixture was concentrated to dryness
2. customThe residue was partitioned into 150 ml Of EtOAc and 100 ml of an aqueous 0.5M solution of K2CO3
3. extractionThe separated aqueous phase was extracted with 50 ml of EtOAc
4. washThe combined organic extracts were successively washed with water (2×50 ml) and brine (50 ml)
5. dry with materialdried over Na2SO4
6. concentrationconcentrated to dryness
7. customThe residue was purified on silica (5% MeOH/CH2Cl2)