Реакция #467393

ord-11261abfa2024092a55d505d66b66827

Уравнение реакции

CC[C@H](C)[C@H](NC(=O)OC)C(=O)N[C@@H](Cc1ccccc1)[C@@H](O)CN(N)Cc1ccc(-c2nccs2)cc1
1-[4-(thiazol-2-yl)-phenyl]-4(S)-hydroxy-2-amino-5(S)-N-(N-methoxycarbonyl-(L)-iso-leucyl)amino-6-phenyl-2-azahexane
CN1CCOCC1
NMM
COC(=O)N[C@H](C(=O)O)C(C)C
N-methoxycarbonyl-(L)-valine
CN(C)C(On1ccccc1=O)=[N+](C)C.F[B-](F)(F)F
TPTU
CC[C@H](C)[C@H](NC(=O)OC)C(=O)N[C@@H](Cc1ccccc1)[C@@H](O)CN(Cc1ccc(-c2nccs2)cc1)NC(=O)[C@@H](NC(=O)OC)C(C)C
1-[4-(Thiazol-2-yl)-phenyl]-4(S)-hydroxy-2-N-(N-methoxycarbonyl-(L)-valyl)amino-5(S)-N-(N-methoxycarbonyl-(L)-iso-leucyl)amino-6-phenyl-2-azahexane

Растворители

Условия реакции

Подробные условия
See reaction.notes.procedure_details.

Методика

Under an argon atmosphere, 321 mg (0.60 mmol) of 1-[4-(thiazol-2-yl)-phenyl]-4(S)-hydroxy-2-amino-5(S)-N-(N-methoxycarbonyl-(L)-iso-leucyl)amino-6-phenyl-2-azahexane (Example 21b) and 182 mg (1.8 mmol) of NMM in 5.8 ml of DMF are added to 126 mg (0.72 mmol) of N-methoxycarbonyl-(L)-valine and 178 mg (0.60 mmol) of TPTU in 3 ml of DMF; the mixture is stirred at room temperature for 15 hours and worked up analogously to Example 3. TLC: Rf=0.15 (methylene chloride/THF 4:1); HPLC20-100: tRet=14.5; FAB MS (M+H)+=697.

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US06300519B1uspto-grants-2001_10