Hydrochloric Acid → HCID 178447157, Verbindung

HRID 1905319Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1905319
C1(CC(CC(=O)NCCC2C=CC=CC=2)C(N(C(=O)[C@H](CC2N=CNC=2)N)N)=O)C2C(=CC=CC=2)C=CC=1.Cl.N(OCCC(C)C)=O.[C:48]1([CH2:58][CH:59]([CH2:75][C:76](=[O:86])[NH:77][CH2:78][CH2:79][C:80]2[CH:85]=[CH:84][CH:83]=[CH:82][CH:81]=2)[C:60]([NH:62][C@H:63]([C:70]([N:72]=[N+]=[N-])=[O:71])[CH2:64][C:65]2[N:69]=[CH:68][NH:67][CH:66]=2)=[O:61])[C:57]2[C:52](=[CH:53][CH:54]=[CH:55][CH:56]=2)[CH:51]=[CH:50][CH:49]=1.[N-]=[N+]=[N-].N[C@@H:91]([CH2:102][CH:103]([CH3:105])[CH3:104])[CH:92]([OH:101])[C:93]([O:95][CH2:96][CH2:97][CH:98]([CH3:100])[CH3:99])=[O:94]>CN(C)C=O.C(N(CC)CC)C>[C:48]1([CH2:58][CH:59]([CH2:75][C:76](=[O:86])[NH:77][CH2:78][CH2:79][C:80]2[CH:85]=[CH:84][CH:83]=[CH:82][CH:81]=2)[C:60]([NH:62][C@H:63]([C:70]([NH:72][C@@H:91]([CH2:102][CH:103]([CH3:105])[CH3:104])[CH:92]([OH:101])[C:93]([O:95][CH2:96][CH2:97][CH:98]([CH3:99])[CH3:100])=[O:94])=[O:71])[CH2:64][C:65]2[N:69]=[CH:68][NH:67][CH:66]=2)=[O:61])[C:57]2[C:52](=[CH:53][CH:54]=[CH:55][CH:56]=2)[CH:51]=[CH:50][CH:49]=1

Komponenten

9

Edukt 6

HCID 313Hydrochloric AcidHCID 8053Isoamyl NitriteHCID 33558AzideHCID 56608254isoamyl (2RS,3S)-3-amino-2-hydroxy-5-methylhexanoateHCID 178511798HCID 178511798, VerbindungHCID 178514640HCID 178514640, Verbindung

Produkt 1

HCID 178447157HCID 178447157, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittel3×HCID 8471TriethylamineLösungsmittel2×

Versuchsvorschrift

To a suspension of 200 mg of N-[(+)-2-(1-naphthylmethyl)-3-(phenethylcarbamoyl)propionyl]-L-histidine hydrazide in 5 ml of N,N-dimethylformamide were added successively dropwise 0.25 ml of a dry 5.1N-hydrogen chloride in N,N-dimethyformamide solution and 0.07 ml of isoamyl nitrite with stirring at -20° C. After disappearance of hydrazide compound, the reaction mixture was cooled to -30° C., and neutralized by adding 0.2 ml of triethylamine to prepare a solution of N-[(+)-2-(1-naphthylmethyl)-3-(phenethylcarbamoyl)-propionyl]-L-histidine azide. The azide solution prepared was added dropwise to 110 mg of isoamyl (2RS,3S)-3-amino-2-hydroxy-5-methylhexanoate and 0.1 ml of triethylamine in 2 ml of dry N,N-dimethylformamide under ice-cooling, and the mixture was stirred for 16 hours. The reaction mixture was evaporated under reduced pressure, and a 5% aqueous sodium bicarbonate solution was added to the residue. The mixture was extracted with ethyl acetate, and the ethyl acetate layer was dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The pressure was purified by silica gel column chromatography (eluent: chloroform/ethanol=10/1 by volume) to obtain 52 mg of isoamyl (2RS,3S)-3-{N-[(+)-2-(1-naphthylmethyl)-3-(phenethylcarbamoyl)propionyl]-L-histidyl}amino-2-hydroxy-5-methylhexanoate as a white powder.

Aufarbeitung

  1. temperaturecooling
  2. customThe reaction mixture was evaporated under reduced pressure
  3. additiona 5% aqueous sodium bicarbonate solution was added to the residue
  4. extractionThe mixture was extracted with ethyl acetate
  5. dry with materialthe ethyl acetate layer was dried over anhydrous magnesium sulfate
  6. customevaporated under reduced pressure
  7. customThe pressure was purified by silica gel column chromatography (eluent: chloroform/ethanol=10/1 by volume)

Quellen und Nachweise

ORD-Eintrag
ord-412eb764db1549d3b0107f8f1c7c0e0c
Quelldatensatz
uspto-grants-1989_06
Patentnummer
US04841067

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