Malic Acid → O-[4-(hexadecylamino)benzoyl]malic acid

HRID 1680290

Reaktionsgleichung

Reaktionsgleichung von HRID 1680290
C([N:11]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[C:12]1[CH:20]=[CH:19][C:15]([C:16](Cl)=[O:17])=[CH:14][CH:13]=1)(OCC1C=CC=CC=1)=O.C(N(CC)CC)C.[C:44]([OH:52])(=[O:51])[CH:45]([CH2:47][C:48]([OH:50])=[O:49])[OH:46].[H][H]>O1CCCC1.CCOCC>[CH2:21]([NH:11][C:12]1[CH:13]=[CH:14][C:15]([C:16]([O:51][C:44](=[O:52])[CH:45]([CH2:47][C:48]([OH:50])=[O:49])[OH:46])=[O:17])=[CH:19][CH:20]=1)[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]

Komponenten

7

Edukt 4

HCID 525Malic AcidHCID 8471TriethylamineHCID 20437379N-carbobenzyloxy-4-(hexadecylamino)benzoyl chlorideHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 86736912O-[4-(hexadecylamino)benzoyl]malic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a warm solution of N-carbobenzyloxy-4-(hexadecylamino)benzoyl chloride and 1.3 g. (1 eq) triethylamine in 100 ml. ether is treated with 2 g. (14.9 m moles) malic acid. An immediate precipitate forms, but the mixture is refluxed for one hour and filtered while hot. The solid is washed several times with hot ether, then the ether is evaporated to yield a white solid. The product is dissolved in tetrahydrofuran (100 ml.) and hydrogenated over 600 mg. 10% Pd(C) at 50 psi until hydrogen uptake stops. The catalyst is filtered, the solution is evaporated, and the residue is crystallized from acetic acid to yield the title compound as a tan, crystalline mass.

Aufarbeitung

  1. temperatureAn immediate precipitate forms, but the mixture is refluxed for one hour
  2. filtrationfiltered while hot
  3. washThe solid is washed several times with hot ether
  4. customthe ether is evaporated
  5. customto yield a white solid
  6. filtrationThe catalyst is filtered
  7. customthe solution is evaporated
  8. customthe residue is crystallized from acetic acid

Quellen und Nachweise

ORD-Eintrag
ord-2af97fe61d724e89897166e735330c5e
Quelldatensatz
uspto-grants-1981_06
Patentnummer
US04272546

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