Ammonium Chloride → methyl 3-[(1S)-1-{[(S)-tert-butylsulfinyl]amino}propyl]benzoate

HRID 64450

Reaktionsgleichung

Reaktionsgleichung von HRID 64450
[C:1]([S@@:5](/[N:7]=[CH:8]/[C:9]1[CH:10]=[C:11]([CH:16]=[CH:17][CH:18]=1)[C:12]([O:14][CH3:15])=[O:13])=[O:6])([CH3:4])([CH3:3])[CH3:2].[CH2:19]([Zn]CC)[CH3:20].CCCCCC.C([Mg]Br)C.C(OCC)C.[Cl-].[NH4+]>C1COCC1.C(OCC)(=O)C>[C:1]([S@@:5]([NH:7][C@H:8]([C:9]1[CH:10]=[C:11]([CH:16]=[CH:17][CH:18]=1)[C:12]([O:14][CH3:15])=[O:13])[CH2:19][CH3:20])=[O:6])([CH3:4])([CH3:2])[CH3:3]

Komponenten

7

Edukt 4

HCID 25517Ammonium ChlorideHCID 90072367methyl 3-[(E)-[(S)-tert-butylsulfinyl]iminomethyl]benzoateHCID 178443585HCID 178443585, VerbindungHCID 178467792HCID 178467792, Verbindung

Produkt 1

HCID 86713465methyl 3-[(1S)-1-{[(S)-tert-butylsulfinyl]amino}propyl]benzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 500 mg of methyl 3-[(E)-{[(S)-tert-butylsulfinyl]imino}methyl]benzoate in 12 ml of THF was added 0.50 ml of a 1 M diethylzinc/hexane solution at −78° C., followed by stirring at the same temperature for 5 minutes. 0.80 ml of a 3 M ethylmagnesium bromide/diethyl ether solution was added thereto at −78° C., followed by stirring at the same temperature for 2 hours. To the reaction mixture were added a saturated aqueous ammonium chloride solution and ethyl acetate to carry out a layer separation operation. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 447 mg of methyl 3-[(1S)-1-{[(S)-tert-butylsulfinyl]amino}propyl]benzoate.

Aufarbeitung

  1. customat −78° C.
  2. stirringby stirring at the same temperature for 2 hours
  3. customa layer separation operation
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-bfc183d973b3464fa90f16ef138d3c7f
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447090B2

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