StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Diisoamyl ketone → (S)-3-(4-Benzyloxy-phenyl)-N-tert-butyl-2-[4-methyl-1-(3-methyl-butyl)-pentylamino]-propionamide monohydrochloride

HRID 430808
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 430808
[ClH:1].[NH2:2][C@@H:3]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:14][CH:13]=1)[C:4]([NH:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].[CH2:26]([C:31]([CH2:33][CH2:34][CH:35]([CH3:37])[CH3:36])=O)[CH2:27][CH:28]([CH3:30])[CH3:29].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>C(Cl)Cl>[ClH:1].[CH2:19]([O:18][C:15]1[CH:14]=[CH:13][C:12]([CH2:11][C@H:3]([NH:2][CH:31]([CH2:26][CH2:27][CH:28]([CH3:30])[CH3:29])[CH2:33][CH2:34][CH:35]([CH3:36])[CH3:37])[C:4]([NH:6][C:7]([CH3:8])([CH3:10])[CH3:9])=[O:5])=[CH:17][CH:16]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 62421Diisoamyl ketoneHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 69584616(S)-2-Amino-3-(4-benzyloxy-phenyl)-N-tert-butyl-propionamide monohydrochloride

Produkt 1

HCID 70218218(S)-3-(4-Benzyloxy-phenyl)-N-tert-butyl-2-[4-methyl-1-(3-methyl-butyl)-pentylamino]-propionamide monohydrochloride
Ausbeute 30,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

(S)-2-Amino-3-(4-benzyloxy-phenyl)-N-tert-butyl-propionamide monohydrochloride (1.04 g, 2.87 mmol, Example 2, Step A) and diisoamyl ketone (0.490 g, 2.87 mmol, Aldrich, Milwaukee, Wis.) were mixed in CH2Cl2 (25 mL). After stirring at ambient temperature under a nitrogen atmosphere for 30 minutes, the solution was cooled to 0° C. in an ice-water bath. To this solution was added sodium triacetoxyborohydride (0.910 g, 4.30 mmol). The resulting reaction mixture was stirred for 30 minutes at 0° C., followed by an additional 12 hours at ambient temperature. Saturated aqueous NaHCO3 solution (25 mL) was added to the reaction mixture, and the resulting mixture was stirred for 5 minutes. The two layers were separated, and the aqueous layer was extracted with CH2Cl2 (2×30 mL). The combined organic solution was dried over Na2SO4. The solution was concentrated in vacuo affording a viscous oil. The crude product was further purified by flash chromatography (25% EtOAc in hexanes). The free amine was dissolved in 10 mL of ethyl ether and treated with ethereal HCl to afford 0.45 g (30%) of the pure titled compound as a white solid; mp 114-115° C.

Aufarbeitung

  1. temperaturethe solution was cooled to 0° C. in an ice-water bath
  2. customThe resulting reaction mixture
  3. stirringwas stirred for 30 minutes at 0° C.
  4. waitfollowed by an additional 12 hours at ambient temperature
  5. stirringthe resulting mixture was stirred for 5 minutes
  6. customThe two layers were separated
  7. extractionthe aqueous layer was extracted with CH2Cl2 (2×30 mL)
  8. dry with materialThe combined organic solution was dried over Na2SO4
  9. concentrationThe solution was concentrated in vacuo
  10. customaffording a viscous oil
  11. customThe crude product was further purified by flash chromatography (25% EtOAc in hexanes)
  12. dissolutionThe free amine was dissolved in 10 mL of ethyl ether
  13. additiontreated with ethereal HCl

Quellen und Nachweise

ORD-Eintrag
ord-d6a0d5c5268042e0bb9efd3103209e32
Quelldatensatz
uspto-grants-2001_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06323243B1

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion