Sodium Carbonate → N1-((S)-1-(4-bromophenyl)ethyl)-5-methyl-3-phenylhex-5-ene-1,3-diamine

HRID 1523258

Reaktionsgleichung

Reaktionsgleichung von HRID 1523258
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]([CH2:18][CH2:19][C:20]([NH:31][S@@](C(C)(C)C)=O)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:21][C:22]([CH3:24])=[CH2:23])C(=O)OC(C)(C)C)[CH3:9])=[CH:4][CH:3]=1.C([O-])([O-])=O.[Na+].[Na+]>Cl.O1CCOCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]([NH:10][CH2:18][CH2:19][C:20]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)([NH2:31])[CH2:21][C:22]([CH3:24])=[CH2:23])[CH3:9])=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 10340Sodium CarbonateHCID 59627246tert-butyl (S)-1-(4-bromophenyl)ethyl(3-((R)-1,1-dimethylethylsulfinamido)-5-methyl-3-phenylhex-5-enyl)carbamate

Produkt 1

HCID 59627223N1-((S)-1-(4-bromophenyl)ethyl)-5-methyl-3-phenylhex-5-ene-1,3-diamineAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 204431481,4-Dioxane hydrochlorideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A mixture of tert-butyl (S)-1-(4-bromophenyl)ethyl(3-((R)-1,1-dimethylethylsulfinamido)-5-methyl-3-phenylhex-5-enyl)carbamate (6.5 g, 0.011 mol) in HCl/dioxane (70 mL) was stirred for 1 hour at 0° C. The mixture was concentrated to give the residue, which was treated with satd aq Na2CO3. The resulting mixture was extracted with EtOAc, and the combined organic layer was concentrated to afford crude N1—((S)-1-(4-bromophenyl)ethyl)-5-methyl-3-phenylhex-5-ene-1,3-diamine (2.97 g, 70%), which was used for the next step without purification.

Aufarbeitung

  1. concentrationThe mixture was concentrated
  2. customto give the residue, which
  3. extractionThe resulting mixture was extracted with EtOAc
  4. concentrationthe combined organic layer was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-14d9d37947034348b849e115f3731500
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09079861B2

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