تفاعل #90713

معادلة التفاعل

ether water

L-homoserine

NaHCO3

Fmoc-OSu

→

N-Fmoc-L-homoserine

المردود 88.0%

المذيبات

water

acetone

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe solution was chilled in an ice bath
2. 2
   workup.ADDITIONwas added
3. 3
   ترشيحthe solid was filtered off
4. 4
   أخرىThe filtrate was separated
5. 5
   غسيلthe aqueous phase was washed with ethyl twice (100 mL×2)
6. 6
   استخلاصThe suspension was extracted with ether (200 mL×2)
7. 7
   غسيلThe combined organic phases were washed with brine once (100 mL)
8. 8
   تجفيفdried over Na2SO4
9. 9
   أخرىAfter evaporation
10. 10
    أخرىwhite solid was obtained (weight: 38 g, yield: 88%)

الإجراء التجريبي

L-homoserine (15 g, MW119.12, 0.126 mol) and NaHCO3 (22 g, MW84, 0.26 mol) were dissolved in water (600 mL). The solution was chilled in an ice bath, followed by addition of Fmoc-OSu (42.5 g, MW337.3, 0.126 mol) in acetone (400 mL). The mixture was stirred overnight. A mixture of ether/water (200 mL/200 mL) was added, and the solid was filtered off. The filtrate was separated and the aqueous phase was washed with ethyl twice (100 mL×2), followed by acidifying with 3N HClaq (about 100 mL) to pH3-4. The suspension was extracted with ether (200 mL×2). The combined organic phases were washed with brine once (100 mL) and dried over Na2SO4. After evaporation, white solid was obtained (weight: 38 g, yield: 88%).

المصدر