Urea → O-(tert-Butyloxycarbonyl-N,O-dimethyl-L-tyrosyl)-N-benzyloxycarbonyl-L-threonine phenacyl ester

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Reaktionsgleichung

[CH2:1]([O:10][C:11](=[O:27])[C@H:12]([C@@H:24]([CH3:26])[OH:25])[NH:13][C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:3].[C:28]([N:35]([CH3:49])[C@H:36]([C:46](O)=[O:47])[CH2:37][C:38]1[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[CH:40][CH:39]=1)([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29].C1CCC(N=C=NC2CCCCC2)CC1.NC(N)=O>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH2:1]([O:10][C:11](=[O:27])[C@H:12]([C@@H:24]([CH3:26])[O:25][C:46](=[O:47])[C@H:36]([CH2:37][C:38]1[CH:39]=[CH:40][C:41]([O:44][CH3:45])=[CH:42][CH:43]=1)[N:35]([C:28]([O:30][C:31]([CH3:33])([CH3:32])[CH3:34])=[O:29])[CH3:49])[NH:13][C:14]([O:16][CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[O:15])[C:2]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)=[O:3]

Komponenten

Reaktionsbedingungen

Temperatur: -30 °C

Versuchsvorschrift

2.00 g (5.38 mmol) of (8), 1.67 g (5.4 mmol) of (9) and 70 mg (0.54 mmol) of DMAP were dissolved in 20 ml of CH2Cl2 and cooled to -30° C., and 1.13 g (5.5 mmol) of DCC were added. The mixture .was allowed to reach RT overnight, the urea was filered off, the filtrate was concentrated, the residue was taken up in ether and left to stand for 1 h, and the urea was again filtered off. Sufficiently pure peptolide (10) was obtained by filtration through silica gel with PE/EA 7/3. Yield: 3.5 g (5.28 mmol, 98%), α!D20 =28.7° (c=0.96, CHCl3)

Aufarbeitung

concentrationthe filtrate was concentrated
waitleft
waitto stand for 1 h
filtrationthe urea was again filtered off

Quellen und Nachweise

ORD-Eintrag: ord-11930512da894a79b50f7e176364c371
Quelldatensatz: uspto-grants-1996_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05504189

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