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Ammonia → Isohexane ethyl acetate

HRID 496634
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 496634
O.O.Cl[Sn]Cl.[CH2:6]([C:13]1[CH:30]=[C:29]([N+:31]([O-])=O)[CH:28]=[CH:27][C:14]=1[C:15]([NH:17][CH:18]([CH2:23][CH2:24][S:25][CH3:26])[C:19]([O:21][CH3:22])=[O:20])=[O:16])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.N.[C:35]([O:38][CH2:39][CH3:40])(=[O:37])[CH3:36]>>[C:35]([O:38][CH2:39][CH3:40])(=[O:37])[CH3:36].[CH3:14][CH2:13][CH2:6][CH:7]([CH3:12])[CH3:8].[NH2:31][C:29]1[CH:28]=[CH:27][C:14]([C:15]([NH:17][C@@H:18]([CH2:23][CH2:24][S:25][CH3:26])[C:19]([O:21][CH3:22])=[O:20])=[O:16])=[C:13]([CH2:6][C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:30]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 222AmmoniaHCID 8857Ethyl AcetateHCID 61436Stannous chloride dihydrateHCID 22321899Methyl 2-[(2-benzyl-4-nitro-benzoyl)amino]-4-methylsulfanyl-butyrate

Produkt 2

HCID 21882781Isohexane ethyl acetateAusbeute 50 %
HCID 57043324
methyl (2S)-2-(4-amino-2-benzyl-benzoylamino)-4-methylsulfanyl-butyrate

Versuchsvorschrift

SnCl2.2H2O (2.5 g, 11.08 mmol) was added to a stirred solution of compound 30 (2.24 mmol) in ethyl acetate(50 mL) and the resulting mixture heated at reflux for 18 h. The reaction mixture was cooled to ambient temperature and treated with 0.880 SG NH3(aq) dropwise to pH8. The resulting precipitate was removed by filtration through diatomaceous earth (Celite®)(545). The filtrates were then evaporated and purified by chromatography (Mega Bond Elut,Silica), eluting with dichloromethane and then 50% ethyl acetate/i-hexane to give the desired compound 21.

Aufarbeitung

  1. temperaturethe resulting mixture heated
  2. temperatureat reflux for 18 h
  3. customThe resulting precipitate was removed by filtration through diatomaceous earth (Celite®)(545)
  4. customThe filtrates were then evaporated
  5. custompurified by chromatography (Mega Bond Elut,Silica)
  6. washeluting with dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-47d19e01bdea473b823dd75d95e1948a
Quelldatensatz
uspto-grants-2005_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06946468B1

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