반응 #67542

반응 방정식

dipeptide

N-(L-phenylalanyl)glycine

Fmoc-glycine

DIEA

HBTU

→

Tripeptide

N-(N-(N-(9-fluorenylmethyloxycarbonyl)-glycyl)L-phenylalanyl)glycine

용매

ethyl acetate

DMF

반응 조건

후처리

1. 1
   workup.STIRRINGthe reaction mixture was stirred for 2 h at 0° C
2. 2
   세척washed with H2O, 1N HCl solution, saturated NaHCO3 solution and saturated NaCl solution
3. 3
   건조The organic layer was dried over MgSO4
4. 4
   여과filtered
5. 5
   농축concentrated to dryness
6. 6
   기타The crude product was purified by silica gel chromatography on a Biotage™ flash chromatography system

실험 절차

To a solution of Fmoc-glycine (297 mg, 1.00 mmol) in DMF (5 mL) at 0° C. was added DIEA (348 μL, 2.00 mmol) and HBTU (379 mg, 1.00 mmol). After stirring for 10 min at 0° C., the resulting activated ester solution was added to crude dipeptide 73 (1.00 mmol) and the reaction mixture was stirred for 2 h at 0° C. It was diluted with ethyl acetate, washed with H2O, 1N HCl solution, saturated NaHCO3 solution and saturated NaCl solution. The organic layer was dried over MgSO4, filtered and concentrated to dryness. The crude product was purified by silica gel chromatography on a Biotage™ flash chromatography system using a gradient of 0-75% ethyl acetate in CH2Cl2. Tripeptide 74 was obtained as a white solid (546 mg, 98%). 1H NMR (400 MHz, CDCl3) δ 1.44 (s, 9H), 3.10 (d, J=6.8 Hz, 2H), 3.74-3.95 (m, 4H), 4.21 (t, J=7.0 Hz, 1H), 4.40 (d, J=7.2 Hz, 2H), 4.70 (q, J=7.5 Hz, 1H), 5.36 (bs, 1H), 6.31 (bs, 1H), 6.53 (d, J=7.4 Hz, 1H), 7.17-7.22 (m, 3H), 7.24-7.28 (m, 2H), 7.30-7.34 (m, 2H), 7.41 (t, J=7.4 Hz, 2H), 7.59 (d, J=7.3 Hz, 2H), 7.77 (d, J=7.3 Hz, 2H).

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