تفاعل #86673

معادلة التفاعل

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

المردود 100.6%

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

المردود 100.6%

المذيبات

DMF

EtOAc

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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%).

المصدر