Triethylamine → HCID 21571524, compound

Temperature

-15 °C

25.6 mg of L-N-[(2S or R)-2-ethylsulfonylmethyl-4-methylpentanoyl]norleucine was dissolved in 0.5 ml of dry DMF, and a dry DMF solution of 30.8 mg of triethylamine, 25.2 mg of DPPA and 38.5 mg of (2RS,3R,4S)-4-amino-5-cyclohexyl-1-morpholino-2,3-pentanediol dihydrochloride was added thereto at -15° C. under stirring. The mixture was stirred at the same temperature for one hour and at room temperature overnight. The reaction solution was diluted with 10 ml of ethyl acetate. The ethyl acetate layer was washed with water and with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue thereby obtained was purified by silica gel column chromatography (chloroform/methanol=50/1) to obtain 21.7 mg of (2S,3R,4S)-4-{L-N-[(2S or R)-2-ethylsulfonylmethyl-4 -methylpentanoyl]norleucyl}amino-5-cyclohexyl-1-morpholino-2,3-pentanediol as colorless solid.

1. stirringThe mixture was stirred at the same temperature for one hour and at room temperature overnight
2. washThe ethyl acetate layer was washed with water and with a saturated sodium chloride aqueous solution
3. dry with materialdried over anhydrous sodium sulfate
4. distillationThe solvent was distilled off under reduced pressure
5. customthe residue thereby obtained
6. customwas purified by silica gel column chromatography (chloroform/methanol=50/1)

ORD record

ord-dd93b2e9abd049b39f539617621681d0

Source dataset

uspto-grants-1996_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05481036