Dicyclohexylcarbodiimide → Boc-beta-cyano-L-alanine

HRID 58896

反応式

HRID 58896 の反応式
C1(N=C=NC2CCCCC2)CCCCC1.[C:16]([NH:23][C@H:24]([C:29]([OH:31])=[O:30])[CH2:25][C:26](=O)[NH2:27])([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17]>CC(C)=O.N1C=CC=CC=1>[C:19]([O:18][C:16]([NH:23][C@@H:24]([CH2:25][C:26]#[N:27])[C:29]([OH:31])=[O:30])=[O:17])([CH3:22])([CH3:21])[CH3:20]

参加物

5

反応物 2

HCID 10868DicyclohexylcarbodiimideHCID 82035N2-((tert-Butoxy)carbonyl)-L-asparagine

生成物 1

HCID 7019873Boc-beta-cyano-L-alanine収率 64.2%

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 1049Pyridine溶媒

実験手順

A solution of dicyclohexylcarbodiimide (DCC, 8.3 g, 40 mmol) in acetone (100 ml) was added dropwise a suspension of Boc-asparagine (9.3 g, 40 mmol) in pyridine (50 mL) at 0° C. under nitrogen. The reaction mixture was stirred at ambient temperature for 3 h. The mixture was filtered and the filtrate was concentrated. The residue was dissolved in dichloromethane (400 mL) and the solution was washed with 2 N aqueous HCl (20 mL×3) and brine (200 mL), dried over anhydrous sodium sulfate, and concentrated to afford (S)-2-(tert-butoxycarbonylamino)-3-cyanopropanoic acid (5.5 g, 56% yield), which was used directly without further purification.

後処理

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. dissolutionThe residue was dissolved in dichloromethane (400 mL)
  4. washthe solution was washed with 2 N aqueous HCl (20 mL×3) and brine (200 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-9fbf77c1d7c74834977d81de168ffeb4
出典データセット
uspto-grants-2016_09
特許番号
US09434761B2

関連ノート

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