Реакция #86673

Уравнение реакции

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

Выход 100.6%

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

Выход 100.6%

Растворители

DMF

EtOAc

Условия реакции

Обработка

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

Методика

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%).

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