反応 #86673

反応方程式

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

収率 100.6%

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

収率 100.6%

溶媒

DMF

EtOAc

反応条件

後処理

1. 1
   洗浄was washed with 1M hydrochloric acid, saturated aqueous NaHCO3 and brine
2. 2
   乾燥The organic layer was dried over MgSO4
3. 3
   その他the solvent was removed in vacuo
4. 4
   その他The crude product was purified by recrystallisation from EtOAc

実験手順

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%).

出典