Dicyclohexylcarbodiimide → Z-Trp-Pro-OBut

HRID 1154157

Reaktionsgleichung

Reaktionsgleichung von HRID 1154157
C1CCC(N=C=NC2CCCCC2)CC1.[NH:16]([C:31]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:32])[C@H:17]([C:28]([OH:30])=O)[CH2:18][C:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[NH:21][CH:20]=1.[NH:41]1[CH2:52][CH2:51][CH2:50][C@H:42]1[C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44].C1C=CC2N(O)N=NC=2C=1>CN(C)C=O>[NH:16]([C:31]([O:33][CH2:34][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)=[O:32])[C@H:17]([C:28]([N:41]1[CH2:52][CH2:51][CH2:50][C@H:42]1[C:43]([O:45][C:46]([CH3:48])([CH3:49])[CH3:47])=[O:44])=[O:30])[CH2:18][C:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[NH:21][CH:20]=1

Komponenten

6

Edukt 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 101176benzyloxycarbonyl-L-tryptophanHCID 6453108L-Proline 1,1-dimethylethyl ester

Produkt 1

HCID 13178803Z-Trp-Pro-OBut

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

10.92 g (53 mmoles) of DCC are added at 0° C. to a solution of 16.9 g (50 mmoles) of Z-Trp-OH, 8.55 g (50 mmoles) of H-Pro-OBut and 6.75 g (50 mmoles) of HOBt in 75 ml of dimethylformamide. The mixture is stirred for 2 hours at 0° C. and left to stand overnight at room temperature. The precipitate is filtered off and the filtrate is concentrated. The residue is worked up analogously to Example 1 a. The residue is triturated with ether. Yield 19.49 g (79%), melting point 173°, [α]D25 =-54.2° (c=1, dimethylformamide).

Aufarbeitung

  1. waitleft
  2. waitto stand overnight at room temperature
  3. filtrationThe precipitate is filtered off
  4. concentrationthe filtrate is concentrated
  5. customThe residue is triturated with ether
  6. customYield 19.49 g (79%), melting point 173°, [α]D25 =-54.2° (c=1, dimethylformamide)

Quellen und Nachweise

ORD-Eintrag
ord-d31d4dc102284d9abf1553600d7eff4d
Quelldatensatz
uspto-grants-1984_12
Patentnummer
US04487764

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