反应详情

温度

25 °C

Dipeptide Fmoc-NH-L-Ile-S-Phe-CH2OH (1b) (2.0 g, 4.11 mmol) was taken in 20% piperidine in DMF (20 mL) and stirred for 15 minutes at 25° C., TLC examination showed complete removal of the Fmoc protecting group (NH2-L-Ile-S-Phe-CH2OH), further confirmed by LC/MS examination, which showed M+−1 (263.3) peak. The reaction mixture was concentrated in vacuo, excess of the piperidine was removed by co-evaporating with toluene (2×20 mL), the free amino dipeptide was further dried over high vacumn for 30 minutes, and then redissolved in dry DMF (5 mL) and added to the mixture of N-(9-fluorenylmethoxycarbonyl)-D-leucine (1.59 g, 4.52 mmol), DCC (931 mg, 4.52 mmol) and HOBt (610.0 mg, 4.52 mmol) in dry DMF (150 mL) at 25° C. The stirring was further continued for 14 h at 25° C. After 14 h white colored crystals precipitated out (DCU), which was filtered. The filterate was checked on TLC (5% MeOH: CH2Cl2) which showed formation of a new compound at higher Rf (0.5), LC/MS also showed molecular ion peak corresponding to the tripeptide 2b with other impurities peaks. The crude product was chromatographed on silica gel (Silica gel 60, 63-200μ) column and eluted with 4% MeOH: CH2Cl2 to give 450 mg of the tripeptide Fmoc-NH-D-Leu-L-Ile-S-Phe-CH2OH (2b) as a white solid. Checked on LC/MS which showed M++1 (600.3) and M++Na (622.3).

1. customremoval of the Fmoc protecting group (NH2-L-Ile-S-Phe-CH2OH)
2. concentrationThe reaction mixture was concentrated in vacuo, excess of the piperidine
3. customwas removed by co-evaporating with toluene (2×20 mL)
4. dry with materialthe free amino dipeptide was further dried over high vacumn for 30 minutes
5. dissolutionredissolved in dry DMF (5 mL)
6. waitThe stirring was further continued for 14 h at 25° C
7. customAfter 14 h white colored crystals precipitated out (DCU), which
8. filtrationwas filtered
9. customThe crude product was chromatographed on silica gel (Silica gel 60, 63-200μ) column
10. washeluted with 4% MeOH