Chloroform → Z-Leu-Phe-CO2Bzl

HRID 1757135Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1757135
[NH:1]([C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22])[C@H:2]([C:7]([NH:9][C@H:10]([C:18]([OH:20])=O)[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].N([C:55]([O:57][CH2:58][C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1)=[O:56])[C@H](C(N[C@H](C(C(OCC)=O)=O)CC1C=CC=CC=1)=O)CC(C)C.C(OCC1C=CC=CC=1)C1C=CC=CC=1.[Na].C(Cl)(Cl)Cl>C(O)C1C=CC=CC=1.CO>[NH:1]([C:21]([O:23][CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)=[O:22])[C@H:2]([C:7]([NH:9][C@H:10]([C:18]([C:55]([O:57][CH2:58][C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1)=[O:56])=[O:20])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5]

Komponenten

7

Edukt 4

HCID 6212ChloroformHCID 7408339Z-Leu-phe-OHHCID 66729449CID 66729449HCID 131719097Z-Leu-Phe-CO2Et

Produkt 1

HCID 131719099Z-Leu-Phe-CO2BzlAusbeute 17 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 244Benzyl AlcoholLösungsmittelHCID 887MethanolLösungsmittel

Versuchsvorschrift

This compound was prepared from Z-Leu-Phe-OH and benzyl oxalyl chloride in 17% yield by the procedure described in the synthesis of Z-Leu-Phe-CO2Et, except that benzyl oxalyl chloride was used in place of ethyl oxalyl chloride and sodium benzyloxide in benzyl alcohol was used for enol ester hydrolysis. Single spot on TLC, Rf =0.63 (CHCl3 :CH3OH=50:1). Pale yellow solid, mp 117°-119° C. MS(FAB) m/e=532 (m+1). H1NMR ok.

Quellen und Nachweise

ORD-Eintrag
ord-dbdb081ab12a4314bb1b24f306d5d73e
Quelldatensatz
uspto-grants-1995_08
Patentnummer
US05444042

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