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

HRID 1479039ノート

反応式

HRID 1479039 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-901456e0fd4c4dee8b6db89cdb067ac6
出典データセット
uspto-grants-2016_08
特許番号
US09403835B2

反応ノート

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