تفاعل #5500

معادلة التفاعل

3-t-Butoxycarbonylmethyl-10-hydroxymethyl-2-oxo-1-azacyclodecane

Triethylamine

Thiolacetic acid

triethylamine

2-fluoro-1-methylpyridinium toluene-4-sulfonate

→

10-(acetylthiomethyl)-3-t-butoxycarbonylmethyl-2-oxo-1-azacyclodecane

المذيبات

benzene

acetone

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةthe reaction is heated
2. 2
   درجة الحرارةto reflux for 2 hours
3. 3
   أخرىThe solvent is then removed
4. 4
   أخرىthe crude product is partitioned between methylene chloride and water
5. 5
   استخلاصthe aqueous phase is extracted several times with methylene chloride
6. 6
   تجفيفThe combined organic layers are dried (MgSO4)
7. 7
   أخرىthe solvent is evaporated
8. 8
   أخرىThe crude product is purified by silica gel chromatography (15% ethyl acetate/hexane)

الإجراء التجريبي

3-t-Butoxycarbonylmethyl-10-hydroxymethyl-2-oxo-1-azacyclodecane (0.50 g, 1.67 mmol) is dissolved in acetone (5.0 mL) and benzene (5.0 mL). Triethylamine (0.26 mL, 1.9 mmol) is added, followed by 2-fluoro-1-methylpyridinium toluene-4-sulfonate (0.54 g, 1.9 mmol), and the reaction is stirred at room temperature for 90 minutes. Thiolacetic acid (0.14 mL, 1.9 mmol) and more triethylamine (0.26 mL, 1.9 mmol) are added, and the reaction is heated to reflux for 2 hours. The solvent is then removed, the crude product is partitioned between methylene chloride and water, and the aqueous phase is extracted several times with methylene chloride. The combined organic layers are dried (MgSO4) and the solvent is evaporated. The crude product is purified by silica gel chromatography (15% ethyl acetate/hexane) to give 10-(acetylthiomethyl)-3-t-butoxycarbonylmethyl-2-oxo-1-azacyclodecane, MS: M+1=358.

المصدر