Reaktion #41505

Reaktionsgleichung

(S)-tert-butyl 1-(methoxy(methyl)amino)-1-oxopropan-2-ylcarbamate

Magnesium

(4-bromo-2-methoxyphenyl)(methyl)sulfane

iodine

→

(R)-t-Butyl 1-(3-methoxy-4-(methylthio)phenyl)-1-oxopropan-2-ylcarbamate

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe tube was sealed
2. 2
   Sonstigeflushed with argon
3. 3
   workup.ADDITIONwas added as a solid
4. 4
   workup.STIRRINGthe mixture was stirred at r.t. for 1 h
5. 5
   SonstigeThen the solvent was evaporated
6. 6
   Sonstigethe mixture was partitioned between aq. HCl (1N) and ethyl acetate
7. 7
   SonstigeThe organic layer was separated
8. 8
   Sonstigedried
9. 9
   SonstigeThe product was isolated by HPLC
10. 10
    Sonstigeto afford 10 mg (10%)

Vorschrift

Magnesium (17 μg, 0.69 mmol) was placed in a screwcap reaction tube, and a solution of (4-bromo-2-methoxyphenyl)(methyl)sulfane (308e, 100 μg, 0.43 mmol) in tetrahydrofuran (1 mL) was added, followed by a small crystal of iodine. The tube was sealed and flushed with argon. The mixture was stirred at 60° C. overnight. After cooling (S)-tert-butyl 1-(methoxy(methyl)amino)-1-oxopropan-2-ylcarbamate (35 μg, 150 μmol) was added as a solid, and the mixture was stirred at r.t. for 1 h. Then the solvent was evaporated, the mixture was partitioned between aq. HCl (1N) and ethyl acetate. The organic layer was separated and dried. The product was isolated by HPLC to afford 10 mg (10%).

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