Reaktion #990122

Reaktionsgleichung

compound

2-(3-Tritylsulfanyl-propyl)-succinic acid 4-tert-butyl ester

HOBt

4-biphenylethylamine

DIC

→

3-(2-Biphenyl-4-yl-ethylcarbamoyl)-6-tritylsulfanyl-hexanoic acid tert-butyl ester

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction mixture was partitioned between HCl (0.5N, excess) and ethyl acetate
2. 2
   ExtraktionThe aqueous phase was extracted several times with ethyl acetate
3. 3
   WaschenThe recombined organic layer was washed with brine, with a saturated sodium hydrogen carbonate solution
4. 4
   SonstigeThe solvent was evaporated
5. 5
   Trocknenfollowing drying over sodium sulfate

Vorschrift

To a solution of the compound of example 29 (200 mg, 0.41 mmol) and HOBt (66 mg, 0.49 mmol) in DMF (2 mL), were added 4-biphenylethylamine (124 mg, 0.62 mmol) and DIC (78 μL) respectively. The reaction mixture was stirred for 24 h at room temperature. The reaction mixture was partitioned between HCl (0.5N, excess) and ethyl acetate. The aqueous phase was extracted several times with ethyl acetate. The recombined organic layer was washed with brine, with a saturated sodium hydrogen carbonate solution, and again with brine. The solvent was evaporated following drying over sodium sulfate, and the crude was flashed using 30% ethyl acetate in hexanes. 1H-NMR (CDCl3, 400 MHz: 1.55(s, 9H); 1.41-1.57(m, 2H); 2.04-2.28(m, 6H); 2.54(m, 1H); 2.80(m, 2H); 3.45-3.55(m, 2H), 5.66(m, 1H); 7.19-7.57(m, 24H).

Quelle