반응 #86673

반응 방정식

DIPEA

(S)-2-[(S)-2-benzyloxycarbonylamino-3-(4-hydroxy-phenyl)-propionylamino]-4-methyl pentanoic acid

methyl ester

(S)-2-Amino-6-hydroxy-hexanoic acid methyl ester

HATU

→

diol

수율 100.6%

(S)-6-Hydroxy-2-{(S)-2-[(S)-3-(4-hydroxy-phenyl)-2-methyl-propionylamino]-4-methyl-pentanoylamino}-hexanoic acid methyl ester

수율 100.6%

용매

DMF

EtOAc

반응 조건

후처리

1. 1
   세척was washed with 1M hydrochloric acid, saturated aqueous NaHCO3 and brine
2. 2
   건조The organic layer was dried over MgSO4
3. 3
   기타the solvent was removed in vacuo
4. 4
   기타The crude product was purified by recrystallisation from EtOAc

실험 절차

To a suspension of (S)-2-[(S)-2-benzyloxycarbonylamino-3-(4-hydroxy-phenyl)-propionylamino]-4-methyl pentanoic acid (Bachem) (5.44 mmol, 1.36 g, 1 eq) and methyl ester 82 (5.44 mmol, 0.91 g) in DMF was added HATU (5.98 mmol, 1.41 g, 1.1 eq). DIPEA (0.12 mol, 1.62 g, 2.1 eq) was added and the reaction mixture was stirred at room temperature overnight. EtOAc (l 00 mL) was added the mixture was washed with 1M hydrochloric acid, saturated aqueous NaHCO3 and brine. The organic layer was dried over MgSO4 and the solvent was removed in vacuo. The crude product was purified by recrystallisation from EtOAc to provide diol 83 as an oil (2.39 g, 76%).

출처