Reaktion #86673

Reaktionsgleichung

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

Ausbeute 100.6%

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

Ausbeute 100.6%

Lösungsmittel

DMF

EtOAc

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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%).

Quelle