반응 #61383

반응 방정식

hydrochloride

cyclopropylmethylamine

triethylamine

Fmoc-β-Ala-OH

oxalyl chloride

→

N-cyclopropylmethyl β-alanine amide

수율 57.4%

용매

dichloromethane

반응 조건

후처리

1. 1
   workup.WAITAfter 10 min
2. 2
   추출the aqueous mixture was extracted with dichloromethane (3×30.0 mL)
3. 3
   농축The organic solution was concentrated in vacuo to dryness
4. 4
   workup.ADDITIONThe residue was treated with a solution of 20% piperidine in N,N-dimethylforamide (20.0 mL) for 0.5 hr
5. 5
   기타After removal of the solvent in vacuo
6. 6
   workup.ADDITIONthe residue was treated with 1 M hydrochloride (20.0 mL) and ethyl acetate (20.0 mL)
7. 7
   기타The mixture was separated
8. 8
   기타The precipitate was removed by filtration
9. 9
   세척eluted with 20% pyridine

실험 절차

To solution of Fmoc-β-Ala-OH (1.0 g, 3.212 mmol) and oxalyl chloride (0.428 g, 0.29 mL, 3.373 mmol) in dichloromethane (20.0 mL) was added a few drops of N,N-dimethylformamide at 0° C. The mixture was stirred at room temperature for 1 hr followed by addition of cyclopropylmethylamine (0.229 g, 0.28 mL, 3.212 mmol) and triethylamine (0.65 g, 0.90 mL, 6.424 mmol). After 10 min, the mixture was treated with 1 M hydrochloride (10.0 mL) and the aqueous mixture was extracted with dichloromethane (3×30.0 mL). The organic solution was concentrated in vacuo to dryness. The residue was treated with a solution of 20% piperidine in N,N-dimethylforamide (20.0 mL) for 0.5 hr. After removal of the solvent in vacuo, the residue was treated with 1 M hydrochloride (20.0 mL) and ethyl acetate (20.0 mL). The mixture was separated and the aqueous layer was basified with solid sodium hydroxide to pH=8. The precipitate was removed by filtration and the aqueous solution was subjected to ion exchange column eluted with 20% pyridine to give 0.262 g (57%) of N-cyclopropylmethyl β-alanine amide. 1H NMR (200 MHz, CD3OD) δ 0.22 (m, 2H), 0.49 (m, 2H), 0.96 (m, 2H), 2.40 (t, 2H), 2.92 (t, 2H), 3.05 (d, 2H); MS (ES): 143.1 (M++1).

출처