Ammonium Chloride → Methyl 5-(1,1-dimethylethylsulfinamido)-5-(2-methoxynaphthalen-1-yl)pentanoate

HRID 594363

Reaktionsgleichung

Reaktionsgleichung von HRID 594363
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[O:12][CH3:13].[Li]CCCC.[C:19]([S:23]([N:25]=[CH:26][CH2:27][CH2:28][CH2:29][C:30]([O:32][CH3:33])=[O:31])=[O:24])([CH3:22])([CH3:21])[CH3:20].[NH4+].[Cl-]>C1COCC1.O.CCOCC>[CH3:21][C:19]([CH3:22])([S:23]([NH:25][CH:26]([C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[O:12][CH3:13])[CH2:27][CH2:28][CH2:29][C:30]([O:32][CH3:33])=[O:31])=[O:24])[CH3:20]

Komponenten

8

Edukt 4

HCID 25517Ammonium ChlorideHCID 728601-Bromo-2-methoxynaphthaleneHCID 74336636Methyl 5-((tert-butylsulfinyl)imino)pentanoateHCID 178418339Butyllithium

Produkt 1

HCID 69082394Methyl 5-(1,1-dimethylethylsulfinamido)-5-(2-methoxynaphthalen-1-yl)pentanoate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

A cooled (−78° C.) solution of commercially available 1-bromo-2-methoxynaphthalene (0.839 g; 2.14 mmol) in anh. THF (20 ml), under nitrogen, was treated dropwise with a solution of 1.6 M n-BuLi in hexanes (1.35 ml; 2.16 mmol). The resulting solution was further stirred at −78° C. for 10 min. A solution of methyl 5-((tert-butylsulfinyl)imino)pentanoate (0.500 g; 2.14 mmol) in anh. THF (2 ml) was then added to the cooled reaction mixture, and stirring at −78° C. was continued for 30 min. The resulting reaction mixture was treated successively with aq. sat. NH4Cl (35 ml), Et2O (75 ml) and water (20 ml). The separated organic layer was then washed with brine (30 ml), dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (DCM/MeOH=15/1) afforded methyl 5-(1,1-dimethylethylsulfinamido)-5-(2-methoxynaphthalen-1-yl)pentanoate as a yellow oil. LC-MS (conditions A): tR=0.83 min. and [M+H]+: 391.93 g/mol.

Aufarbeitung

  1. stirringstirring at −78° C.
  2. waitwas continued for 30 min
  3. customThe resulting reaction mixture
  4. washThe separated organic layer was then washed with brine (30 ml)
  5. dry with materialdried over anh. MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure
  8. customPurification by FC (DCM/MeOH=15/1)

Quellen und Nachweise

ORD-Eintrag
ord-1533716df6f3407faf8f810d4fada3d5
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242970B2

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