反应 #40505

反应方程式

water

DCM

(S)-4-((S)-2-Amino-propyl)-6,6-dimethyl-morpholine-3 carboxylic acid (6-chloro-9H-beta-carbolin-8-yl)-amide hydrochloride salt

methyl chloroformate

→

desired product

收率 77.0%

{(S)-2-[(S)-5-(6-Chloro-9H-beta-carbolin-8-ylcarbamoyl)-2,2-dimethyl-morpholin-4-yl]-1-methyl-ethyl}-carbamic acid methyl ester

收率 77.0%

溶剂

pyridine

反应条件

后处理

1. 1
   浓缩the mixture was concentrated to dryness
2. 2
   其他The residue was partitioned into 150 ml Of EtOAc and 100 ml of an aqueous 0.5M solution of K2CO3
3. 3
   萃取The separated aqueous phase was extracted with 50 ml of EtOAc
4. 4
   洗涤The combined organic extracts were successively washed with water (2×50 ml) and brine (50 ml)
5. 5
   干燥dried over Na2SO4
6. 6
   浓缩concentrated to dryness
7. 7
   其他The residue was purified on silica (5% MeOH/CH2Cl2)

实验过程

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.

来源