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

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.

1. temperaturecooled to 0° C.
2. stirringAfter stirring at 0° C. for 1 hour and at room temperature for 2 hours
3. customthe mixture was partitioned between ethyl acetate and 0.5N hydrochloric acid
4. extractionsubsequently extracted three times with ethyl acetate
5. washThe pooled ethyl acetate extracts were washed in succession with water, saturated sodium bicarbonate, and brine
6. dry with materialdried (sodium sulfate)
7. filtrationfiltered
8. customto give 5.77 g

ORD-Eintrag

ord-32b402f60fe74c78b310c537e44ff646

Quelldatensatz

uspto-grants-1998_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05723602