Methyl iodide → methyl N-(tert-butoxycarbonyl)-N-(2-cyanoethyl)-2-methylalaninate

HRID 1479039노트

반응식

HRID 1479039 반응식
[CH3:1]I.[C:3]([O:7][C:8]([N:10]([CH2:17][CH2:18][C:19]#[N:20])[C:11]([CH3:16])([CH3:15])[C:12]([OH:14])=[O:13])=[O:9])([CH3:6])([CH3:5])[CH3:4]>CN(C=O)C>[C:3]([O:7][C:8]([N:10]([CH2:17][CH2:18][C:19]#[N:20])[C:11]([CH3:15])([CH3:16])[C:12]([O:14][CH3:1])=[O:13])=[O:9])([CH3:6])([CH3:5])[CH3:4]

참가 물질

4

반응물 2

HCID 6328Methyl iodideHCID 575236442-((tert-Butoxycarbonyl)(2-cyanoethyl)amino)-2-methylpropanoic acid

생성물 1

HCID 57523645methyl N-(tert-butoxycarbonyl)-N-(2-cyanoethyl)-2-methylalaninate수율 95%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Methyl iodide (12.5 mL, 193.2 mmol) was added to a mixture of 2-[(tert-butoxycarbonyl)(2-cyanoethyl)amino]-2-methylpropanoic acid (16.5 g, 64.4 mmol) and KHCO3 (12.9 g, 193.2 mmol) in DMF (150 mL) and the reaction mixture was stirred at room temperature for 16 hours. After dilution with water, the solution was extracted with a 1/1 mixture of hexane/EA (2×). The combined organics were dried over magnesium sulfate and concentrated in vacuo to afford the title compound (16.5 g, 95%) as a yellow oil. 1H NMR (DMSO-d6) δ 3.61-3.55 (m, 5H), 2.71 (t, J=6.76 Hz, 2H), 1.42-1.36 (m, 15H).

후처리

  1. extractionAfter dilution with water, the solution was extracted with a 1/1 mixture of hexane/EA (2×)
  2. dry with materialThe combined organics were dried over magnesium sulfate
  3. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-901456e0fd4c4dee8b6db89cdb067ac6
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09403835B2

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