反応 #67542

反応方程式

dipeptide

N-(L-phenylalanyl)glycine

Fmoc-glycine

DIEA

HBTU

→

Tripeptide

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

溶媒

ethyl acetate

DMF

反応条件

後処理

1. 1
   workup.STIRRINGthe reaction mixture was stirred for 2 h at 0° C
2. 2
   洗浄washed with H2O, 1N HCl solution, saturated NaHCO3 solution and saturated NaCl solution
3. 3
   乾燥The organic layer was dried over MgSO4
4. 4
   ろ過filtered
5. 5
   濃縮concentrated to dryness
6. 6
   その他The crude product was purified by silica gel chromatography on a Biotage™ flash chromatography system

実験手順

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).

出典