Hydrochloric Acid → HCID 178447098, Verbindung

HRID 1905325Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1905325
[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-].[CH2:90]([O:95][CH2:96][CH:97]([OH:104])[C@@H:98](N)[CH2:99][CH:100]([CH3:102])[CH3:101])[CH2:91][CH:92]([CH3:94])[CH3:93].C(=O)(O)[O-].[Na+]>CN(C)C=O.C(N(CC)CC)C>[CH2:90]([O:95][CH2:96][CH:97]([OH:104])[C@@H:98]([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)[CH2:99][CH:100]([CH3:102])[CH3:101])[CH2:91][CH:92]([CH3:94])[CH3:93]

Komponenten

10

Edukt 7

HCID 313Hydrochloric AcidHCID 8053Isoamyl NitriteHCID 33558AzideHCID 516892Sodium BicarbonateHCID 86743184(2RS, 3S)-3-amino-2-hydroxy-5-methylhexyl isoamyl etherHCID 178511798HCID 178511798, VerbindungHCID 178514640HCID 178514640, Verbindung

Produkt 1

HCID 178447098HCID 178447098, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittel3×HCID 8471TriethylamineLösungsmittel2×

Versuchsvorschrift

To a solution of 115 mg of N-[(+)-2-(1-naphthylmethyl)-3-(phenethylcarbamoyl)propionyl]-L-histidine hydrazide in 2 ml of N,N-dimethylformamide were added successively dropwise 0.16 ml of a dry 5.1N-hydrogen chloride in N,N-dimethylformamide solution and 0.04 ml of isoamyl nitrite under ice-cooling, and mixture was stirred. After disappearance of hydrazide compound, the reaction mixture was cooled to -30° C., and neutralized by adding 0.11 ml of triethylamine to prepare a solution of N-[(+)-2-(1-naphthylmethyl)-3-(phenethylcarbamoyl)propionyl]-L-histidine azide. The azide solution was added dropwise to a solution of 63 mg of (2RS, 3S)-3-amino-2-hydroxy-5-methylhexyl isoamyl ether and 0.035 ml of triethylamine in 2 ml of N,N-dimethylformamide solution 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 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/water32 8/3/1 by volume) to obtain 51 mg of (2RS, 3S)-3-{N-[(+)-2-(1-naphthylmethyl)-3-(phenethylcarbamoyl)-propionyl]-L-histidyl}amino-2-hydroxy-5-methylhexyl isoamyl ether as a white powder.

Aufarbeitung

  1. temperaturecooling
  2. stirringthe mixture was stirred for 16 hours under ice-
  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 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/water32 8/3/1 by volume)

Quellen und Nachweise

ORD-Eintrag
ord-8b86088f0ca041cb94e2e2afe20c7e1e
Quelldatensatz
uspto-grants-1989_06
Patentnummer
US04841067

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