تفاعل #41505

معادلة التفاعل

(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

المذيبات

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   أخرىThe tube was sealed
2. 2
   أخرىflushed 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
   أخرىThen the solvent was evaporated
6. 6
   أخرىthe mixture was partitioned between aq. HCl (1N) and ethyl acetate
7. 7
   أخرىThe organic layer was separated
8. 8
   أخرىdried
9. 9
   أخرىThe product was isolated by HPLC
10. 10
    أخرىto afford 10 mg (10%)

الإجراء التجريبي

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%).

المصدر