Reaktion #1058749

ord-ff1444235c2645ed938a84676f0667fc

Reaktionsgleichung

COC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](NC(=O)[C@H](Cc1ccc(OC(C)(C)C)cc1)NC(=O)[C@@H](NC(=O)OCc1ccccc1)[C@@H](C)OC(C)(C)C)[C@@H](C)OC(C)(C)C
Z-Thr(tBu)-Tyr(tBu)-Thr(tBu)-Gln-Asn-Phe-OCH3
NN.O
hydrazine hydrate
→
C[C@@H](OC(C)(C)C)[C@H](NC(=O)OCc1ccccc1)C(=O)N[C@@H](Cc1ccc(OC(C)(C)C)cc1)C(=O)N[C@H](C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](Cc1ccccc1)C(=O)NN)[C@@H](C)OC(C)(C)C
Z-Thr(tBu)-Tyr(tBu)-Thr(tBu)-Gln-Asn-Phe-NH-NH2

Edukte

COC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](NC(=O)[C@H](Cc1ccc(OC(C)(C)C)cc1)NC(=O)[C@@H](NC(=O)OCc1ccccc1)[C@@H](C)OC(C)(C)C)[C@@H](C)OC(C)(C)C
Z-Thr(tBu)-Tyr(tBu)-Thr(tBu)-Gln-Asn-Phe-OCH3
NN.O
hydrazine hydrate

Reagenzien

Keine

Lösungsmittel

CO
methanol

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    FiltrationThe precipitate is filtered off
  2. 2
    Waschenwashed with methanol
  3. 3
    Trocknendried in a high vacuum over concentrated sulfuric acid
  4. 4
    Sonstige[α]D20 = + 4° (c = 0.89 in dimethylformamide)

Vorschrift

2.0 g of Z-Thr(tBu)-Tyr(tBu)-Thr(tBu)-Gln-Asn-Phe-OCH3 are dissolved in 150 ml of methanol and caused to react with 10.7 ml of hydrazine hydrate for 6 hours at room temperature. The precipitate is filtered off, washed with methanol, and dried in a high vacuum over concentrated sulfuric acid. Melting point 231° (decomp); [α]D20 = + 4° (c = 0.89 in dimethylformamide).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04159981uspto-grants-1979_07