Ethylmorpholine → HCID 54209367, Verbindung

HRID 2308769Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2308769
C1(N=C=NC2CCCCC2)CCCCC1.[CH:16]1([C:21]([OH:23])=O)[CH2:20][CH2:19][CH2:18][CH2:17]1.C1(C)C(S(O)(=O)=O)=CC=CC=1.C([O:39][C:40](=[O:51])[C@H:41]([CH2:43][C:44]1[CH:49]=[CH:48][C:47]([Cl:50])=[CH:46][CH:45]=1)[NH2:42])(C)(C)C.C(N1CCOCC1)C>ClCCl.CN(C)C=O>[CH:16]1([C:21]([NH:42][C@H:41]([C:40]([OH:51])=[O:39])[CH2:43][C:44]2[CH:45]=[CH:46][C:47]([Cl:50])=[CH:48][CH:49]=2)=[O:23])[CH2:17][CH2:18][CH2:19][CH2:20]1

Komponenten

7

Edukt 4

HCID 7525EthylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 18840Cyclopentanecarboxylic acidHCID 86741768HCID 86741768, Verbindung

Produkt 1

HCID 54209367HCID 54209367, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A cool solution of 15 mmoles of dicyclohexylcarbodiimide in dichloromethane is added to a solution of 15 mmoles of cyclopentanecarboxylic acid in dichloromethane at -5° C. 15 mmoles of 4-chloro-phenylalanine t-butyl ester toluenesulfonate salt in dimethylformamide (DMF), which is neutralized with N-ethyl morpholine, is then added. The reaction mixture is stirred at 0° C. initially and then at room temperature until the reaction is completed as judged by TLC. Dicyclohexylurea is removed by filtration and 50 ml of ethyl acetate is added to the filtrate. The organic phase is washed until neutral, dried over anhydrous MgSO4 and filtered. The solvent is removed with a rotary evaporator. The residue is crystallized from isopropanol and hexane.

Aufarbeitung

  1. additionis then added
  2. customat room temperature
  3. customDicyclohexylurea is removed by filtration and 50 ml of ethyl acetate
  4. additionis added to the filtrate
  5. washThe organic phase is washed until neutral,
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationfiltered
  8. customThe solvent is removed with a rotary evaporator
  9. customThe residue is crystallized from isopropanol and hexane

Quellen und Nachweise

ORD-Eintrag
ord-6c5c5c6dd18f469694968e9b0c8e754a
Quelldatensatz
uspto-grants-1987_09
Patentnummer
US04690936

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