反応 #40505

反応方程式

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

収率 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

収率 77.0%

溶媒

pyridine

反応条件

後処理

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

実験手順

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.

出典