Reaktion #1574076

Reaktionsgleichung

4-carbamimidamidobenzoyl chloride hydrochloride

4-Carbamimidamidobenzoyl chloride hydrochloride

di-tert-butyl N-(3-(2-(5-(tert-butoxycarbonyl)-5-(2-tert-butoxy-2-oxoethyl)-4,5-dihydro-1,2-oxazol-3-yl)-4-hydroxyphenyl)propanoyl)-L-aspartate

pyridine

sodium bicarbonate

→

title compound

Ausbeute 23.4%

Di-tert-butyl N-(3-(2-(5-(tert-butoxycarbonyl)-5-(2-tert-butoxy-2-oxoethyl)-4,5-dihydro-1,2-oxazol-3-yl)-4-((4-carbamimidamidobenzoyl)oxy)phenyl)propanoyl)-L-aspartate

Ausbeute 23.4%

Lösungsmittel

water acetonitrile

NMP

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe obtained mixture was stirred overnight at 50 C
2. 2
   Extraktionfollowed by extraction with ethyl acetate
3. 3
   TrocknenThe extract was dried over anhydrous magnesium sulfate
4. 4
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure

Vorschrift

4-Carbamimidamidobenzoyl chloride hydrochloride (53.3 mg) was added to a mixture of di-tert-butyl N-(3-(2-(5-(tert-butoxycarbonyl)-5-(2-tert-butoxy-2-oxoethyl)-4,5-dihydro-1,2-oxazol-3-yl)-4-hydroxyphenyl)propanoyl)-L-aspartate (154 mg), pyridine (0.12 mL), and NMP (0.12 mL) at 50 C, and the obtained mixture was stirred at 50 C for 30 minutes. Further, 4-carbamimidamidobenzoyl chloride hydrochloride (53.3 mg) was added thereto, and the obtained mixture was stirred overnight at 50 C. The reaction mixture was fractionated by HPLC (C18, mobile phase: water/acetonitrile (system containing 0.1% TFA)). To the obtained fraction, a saturated aqueous solution of sodium bicarbonate was added, followed by extraction with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain the title compound (44.6 mg).

Quelle