Hydrochloric Acid → HCID 178446399, Verbindung

HRID 1905329Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1905329
[C:1]1([CH2:11][CH:12]([CH2:27][C:28](=[O:38])[NH:29][CH2:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:13](N(C(=O)[C@H](CC2N=CNC=2)N)N)=[O:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.Cl.N(OCCC(C)C)=O.C1(CC(CC(=O)NCCC2C=CC=CC=2)C([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)C2C(=CC=CC=2)C=CC=1.[N-]=[N+]=[N-].Cl.Cl.[CH2:92]([NH:97][CH2:98][CH:99]([OH:106])[C@@H:100](N)[CH2:101][CH:102]([CH3:104])[CH3:103])[CH2:93][CH:94]([CH3:96])[CH3:95].C(=O)(O)[O-].[Na+]>CN(C)C=O.C(N(CC)CC)C>[CH2:92]([NH:97][CH2:98][CH:99]([OH:106])[C@@H:100]([NH:72][C:70](=[O:71])[C@H:63]([CH2:64][C:65]1[N:69]=[CH:68][NH:67][CH:66]=1)[NH:62][C:13](=[O:14])[CH:12]([CH2:11][C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1)[CH2:27][C:28](=[O:38])[NH:29][CH2:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH2:101][CH:102]([CH3:104])[CH3:103])[CH2:93][CH:94]([CH3:96])[CH3:95]

Komponenten

10

Edukt 7

HCID 313Hydrochloric AcidHCID 8053Isoamyl NitriteHCID 33558AzideHCID 516892Sodium BicarbonateHCID 86743185(2RS, 3S)-N-isoamyl-3-amino-2-hydroxy-5-methylhexylamine dihydrochlorideHCID 178511798HCID 178511798, VerbindungHCID 178514640HCID 178514640, Verbindung

Produkt 1

HCID 178446399HCID 178446399, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittel3×HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To a solution of 64 mg of N-[(+)-2-(1-naphthylmethyl)-3-(phenethylcarbamoyl)propionyl]-L-histidine hydrazide in 2 ml of N,N-dimethylformamide were added successively dropwise 0.09 ml of a dry 5.1N-hydrogen chloride in N,N-dimethylformamide solution and 0.022 ml of isoamyl nitrite at -20° C., and the mixture was stirred under ice-cooling. After disappearance hydrazide compound, the reaction mixture was cooled to -30° C., and neutralized by adding 0.063 ml of triethylamine to prepare a solution of N-[(+)-2-(1-naphthylmethyl)-3-(phenethylcarbamoyl)propionyl]--histidine azide. The azide solution was added dropwise to a solution of 40 mg of (2RS, 3S)-N-isoamyl-3-amino-2-hydroxy-5-methylhexylamine dihydrochloride in 2 ml of N,N-dimethylformamide under ice-cooling, and the mixture was stirred for 16 hours under ice-cooling. A 5% aqueous sodium bicarbonate solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, and evaporated under reduced pressure. The residue was purified by preparative silica gel thin layer chromatography (developing solvent: lower layer of chloroform/methanol/water=8/3/1 by volume) to obtain 8 mg of (2RS, 3S)-N-isoamyl-3-{N-[(+)-2-(1-naphthylmethyl)-3-(phenethylcarbamoyl)propionyl]-L-histidyl}amino-2-hydroxy-5-methylhexylamine as a white powder.

Aufarbeitung

  1. temperaturecooling
  2. temperaturecooling
  3. temperaturecooling
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with a saturated sodium chloride aqueous solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated under reduced pressure
  8. customThe residue was purified by preparative silica gel thin layer chromatography (developing solvent: lower layer of chloroform/methanol/water=8/3/1 by volume)

Quellen und Nachweise

ORD-Eintrag
ord-5662c9bf152e48d487d67d105c80b219
Quelldatensatz
uspto-grants-1989_06
Patentnummer
US04841067

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