反応 #41505

反応方程式

(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

溶媒

tetrahydrofuran

反応条件

後処理

1. 1
   その他The tube was sealed
2. 2
   その他flushed 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
   その他Then the solvent was evaporated
6. 6
   その他the mixture was partitioned between aq. HCl (1N) and ethyl acetate
7. 7
   その他The organic layer was separated
8. 8
   その他dried
9. 9
   その他The product was isolated by HPLC
10. 10
    その他to afford 10 mg (10%)

実験手順

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%).

出典