反応 #1288

反応方程式

glycine, ethyl ester, hydrochloride salt

4-methyl morpholine

(S)-2-phthalimido-6-hydroxyhexanoic acid

hydroxybenzotriazole

→

title product

(S)-N-(2-Phthalimido-1-oxohexyl)glycine, ethyl ester

溶媒

dimethylformamide

反応条件

後処理

1. 1
   温度cooled to 0° C.
2. 2
   workup.STIRRINGAfter stirring at 0° C. for 1 hour and at room temperature for 2 hours
3. 3
   その他the mixture was partitioned between ethyl acetate and 0.5N hydrochloric acid
4. 4
   抽出subsequently extracted three times with ethyl acetate
5. 5
   洗浄The pooled ethyl acetate extracts were washed in succession with water, saturated sodium bicarbonate, and brine
6. 6
   乾燥dried (sodium sulfate)
7. 7
   ろ過filtered
8. 8
   その他to give 5.77 g

実験手順

A slurry of glycine, ethyl ester, hydrochloride salt (2.718 g, 19.5 mmol.) in dimethylformamide (36 ml.) was treated with 4-methyl morpholine (2.60 ml., 2.39 g., 23.6 mmol.) and stirred at room temperature for 5 minutes. The mixture was then treated with (S)-2-phthalimido-6-hydroxyhexanoic acid (4.50 g., 16.2 mmol.) and hydroxybenzotriazole (2.225 g., 16.5 mmol.), cooled to 0° C., and then treated with ethyl-3-(3-dimethylamino)propyl carbodiimide, hydrochloride salt (3.438 g., 17.9 mmol.). After stirring at 0° C. for 1 hour and at room temperature for 2 hours, the mixture was partitioned between ethyl acetate and 0.5N hydrochloric acid and subsequently extracted three times with ethyl acetate. The pooled ethyl acetate extracts were washed in succession with water, saturated sodium bicarbonate, and brine, then dried (sodium sulfate), filtered and stripped to give 5.77 g. of title product as a colorless oil. TLC (ethyl acetate) Rf =0.34.

出典