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Ethylmorpholine → HCID 178502932, Verbindung

HRID 476706
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 476706
[ClH:1].C(OC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N)C.[CH3:18][O:19][P:20](CC(CC(C)C)C(O)=O)([CH2:22][N:23]1[C:27](=[O:28])[C:26]2=[CH:29][CH:30]=[CH:31][CH:32]=[C:25]2[C:24]1=[O:33])=[O:21].OC1C2N=NNC=2C=CC=1.C(N1CCOCC1)C.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O>[ClH:1].[CH3:18][O:19][PH:20]([CH2:22][N:23]1[C:27](=[O:28])[C:26]2=[CH:29][CH:30]=[CH:31][CH:32]=[C:25]2[C:24]1=[O:33])=[O:21]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 5

HCID 7525EthylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 200630192(RS)-[[(RS)-(methoxy)(phthalimidomethyl)phosphinyl]methyl]-4-methylvaleric acidHCID 86743560L-leucyl-L-alanine ethyl ester hydrochlorideHCID 178418300HCID 178418300, Verbindung

Produkt 1

HCID 178502932
HCID 178502932, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

1.06 g of L-leucyl-L-alanine ethyl ester hydrochloride and 1.46 g of 2(RS)-[[(RS)-(methoxy)(phthalimidomethyl)-phosphinyl]methyl]-4-methylvaleric acid, prepared as described in Example 1(A)(iii), were dissolved in 12 ml of dimethylformamide. The solution was cooled to 0° C. Thereafter, 1.08 g of hydroxybenzotriazole and 0.46 g of N-ethylmorpholine were added and, after all of the solids had dissolved, 0.88 g of N,N'-dicyclohexylcarbodiimide was added. The mixture was stirred at room temperature for 18 hours. The solvent was then removed by evaporation. The residue was triturated with 50 ml of ethyl acetate and the mixture was filtered in order to remove dicyclohexylurea. The filtrate was washed twice with 50 ml of saturated sodium hydrogen carbonate solution each time, dried over anhydrous sodium sulfate and evaporated to give a yellow gum. This gum was purified by flash chromatography using ethyl acetate for the elution. There were obtained 1.06 g of [(R or S)-2-[[(S)-1-[[(S)-1-(ethoxycarbonyl)ethyl]carbamoyl]-3-methyl-butyl]carbamoyl]-4-methylpentyl](phthalimidomethyl)phosphinic acid methyl ester hydrochloride in the form of a white foam.

Aufarbeitung

  1. dissolutionafter all of the solids had dissolved
  2. customThe solvent was then removed by evaporation
  3. customThe residue was triturated with 50 ml of ethyl acetate
  4. filtrationthe mixture was filtered in order
  5. customto remove dicyclohexylurea
  6. washThe filtrate was washed twice with 50 ml of saturated sodium hydrogen carbonate solution each time
  7. dry with materialdried over anhydrous sodium sulfate
  8. customevaporated
  9. customto give a yellow gum
  10. customThis gum was purified by flash chromatography
  11. washfor the elution

Quellen und Nachweise

ORD-Eintrag
ord-73215da395db4994a9c51fb45e4ab256
Quelldatensatz
uspto-grants-1989_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04885283

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