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Malic Acid → O-{4-[15-(Trifluoromethyl)pentadecylamino]benzoyl}malic acid

HRID 1105905
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1105905
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][C:36]([F:39])([F:38])[F:37])[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:47]([OH:55])(=[O:54])[CH:48]([CH2:50][C:51]([OH:53])=[O:52])[OH:49].[H][H]>O1CCCC1.[Pd].CCOCC>[F:37][C:36]([F:38])([F:39])[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][NH:11][C:12]1[CH:20]=[CH:19][C:15]([C:16]([O:54][C:47](=[O:55])[CH:48]([CH2:50][C:51]([OH:53])=[O:52])[OH:49])=[O:17])=[CH:14][CH:13]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 525Malic AcidHCID 8471TriethylamineHCID 128316114-[N-carbobenzyloxy-15-(trifluoromethyl)pentadecylamino]benzoyl chlorideHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 86737003O-{4-[15-(Trifluoromethyl)pentadecylamino]benzoyl}malic acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938
Palladium
Katalysator
HCID 3283Diethyl EtherLösungsmittel
HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A warm solution of 4-[N-carbobenzyloxy-15-(trifluoromethyl)pentadecylamino]benzoyl chloride and 1.3 g. triethylamine in 100 ml. ether is treated with 2 g. 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% palladium-on-carbon at 50 psi until hydrogen uptake stops. The catalyst is filtered, and the solution is evaporated. The residue is crystallized from acetic acid to yield the product as a white solid.

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-c3fe8e8cf49246fbb39e426f2ae43fa1
Quelldatensatz
uspto-grants-1982_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04310545

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