반응 #1453068

ord-e1f3febee43941949c08619364c34604

반응 방정식

Cc1ccc(S(=O)(=O)O)cc1.N[C@H](CCc1ccccc1)C(=O)OCc1ccccc1
D-Homophenylalanine Benzyl ester Tosylate
O=C([O-])O.[Na+]
sodium bicarbonate
N[C@H](CCc1ccccc1)C(=O)OCc1ccccc1
D-Homophenylalanine Benzyl ester

반응 조건

온도
25°CELSIUS
상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    추출The water layer was extracted with ethyl acetate (3×10 mL)
  2. 2
    추출The combined organic extract
  3. 3
    건조was dried over anhydrous sodium sulfate
  4. 4
    여과filtered
  5. 5
    농축concentrated to dryness

실험 절차

D-Homophenylalanine Benzyl ester Tosylate (2.48 g, 5.6 mmol) was suspended in ethyl acetate (25 mL) and a saturated solution of sodium bicarbonate in water was added in portions (25 mL) with stirring at 25° C. The water layer was extracted with ethyl acetate (3×10 mL). The combined organic extract was dried over anhydrous sodium sulfate, filtered and concentrated to dryness to afford D-Homophenylalanine Benzyl ester. The ester was dissolved in acetonitile (25 mL). NaNd-bis-Boc-L-Ornithine (2.0 g, 6.0 mmol) was then added followed by N-hydroxysuccinimide (50 mg) and dicyclohexylcarbodiimide (1.28 g, 6.2 mmol). The reaction was stirred at 25° C. for 30 hr, filtered and the filtrate concentrated to dryness to afford crude product. It was purified by column chromatography on silica gel (hexane:ethyl acetate=3:1), which gave the title product (2.80 g) as white solid.

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US07893020B2uspto-grants-2011_02