Dicyclohexylcarbodiimide → HCID 21571524, compound

Temperature

0 °C

50 mg of L-N-[(2S or R)-3-(2-hydroxyethyl)-sulfonyl-2-(1-naphthylmethyl)propionyl]norleucine was dissolved in 0.2 ml of dry DMF, and 28.2 mg of 1-hydroxybenzotriazole and 13.2 mg of DCC were added thereto at 0° C. under stirring. Then, 55.2 mg of (2RS,3R,4S)-4-amino-5-cyclohexyl-1-morpholino-2,3-pentanediol dihydrochloride was dissolved in 0.2 ml of dry DMF, and 31.1 mg of triethylamine was added thereto for neutralization. This mixture was added to the previous reaction solution, and the mixture was stirred at 0° C. for two hours and at room temperature overnight. The precipitated dicyclohexyl urea was removed by filtration, and the filtrate was diluted with 10 ml of ethyl acetate. The ethyl acetate layer was washed sequentially with a 4% sodium hydrogencarbonate aqueous solution, with water and with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. Then, the solvent was distilled off. The residue was purified by silica gel column chromatography chloroform/methanol= 20/1) to obtain 20.1 mg of 2S,3R,4S)-4-{L-N-[(2S or R)-3-(2-hydroxyethyl)sulfonyl-2-(1 -naphthylmethyl)propionyl]norleucyl}amino-5-cyclohexyl-1-morpholino-2,3-pentanediol as colorless solid.

1. additionThis mixture was added to the previous reaction solution
2. stirringthe mixture was stirred at 0° C. for two hours and at room temperature overnight
3. customThe precipitated dicyclohexyl urea was removed by filtration
4. additionthe filtrate was diluted with 10 ml of ethyl acetate
5. washThe ethyl acetate layer was washed sequentially with a 4% sodium hydrogencarbonate aqueous solution, with water and with a saturated sodium chloride aqueous solution
6. dry with materialdried over anhydrous sodium sulfate
7. distillationThen, the solvent was distilled off
8. customThe residue was purified by silica gel column chromatography chloroform/methanol= 20/1)

ORD record

ord-2438fedce772472e996cb7d21018b3e1

Source dataset

uspto-grants-1996_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05481036