تفاعل #168341

معادلة التفاعل

Triethylamine

(2R,3R)-3-(benzylamino)pentan-2-ol

2-chloroacetyl chloride

→

N-benzyl-2-chloro-N-((2R,3R)-2-hydroxypentan-3-yl)acetamide

المذيبات

dichloromethane

ظروف التفاعل

المعالجة

1. 1
   أخرىquenched with saturated NaHCO3 solution
2. 2
   أخرىThe layers were separated
3. 3
   استخلاصthe aqueous layer was extracted with dichloromethane (3×10 mL)
4. 4
   غسيلThe combined organic layers were washed with brine
5. 5
   تجفيفdried over anhydrous Na2SO4
6. 6
   ترشيحfiltered
7. 7
   تركيزconcentrated in vacuo
8. 8
   أخرىPurification of the residue on a silica gel column (0 to 50% EtOAc/hexanes)

الإجراء التجريبي

Triethylamine (0.43 mL, 3.4 mmol) was added to a −40° C. solution of (2R,3R)-3-(benzylamino)pentan-2-ol (220 mg, 1.1 mmol) in dichloromethane (100 mL), followed by the addition of 2-chloroacetyl chloride (0.10 mL, 1.1 mmol) dropwise. The reaction mixture was stirred at −40° C. for 1 hour and then quenched with saturated NaHCO3 solution. The layers were separated, and the aqueous layer was extracted with dichloromethane (3×10 mL). The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. Purification of the residue on a silica gel column (0 to 50% EtOAc/hexanes) afforded N-benzyl-2-chloro-N-((2R,3R)-2-hydroxypentan-3-yl)acetamide. MS APCl calc'd for C14H20ClNO2 [M+H]+ 270. found 270.

المصدر