1,1'-Carbonyldiimidazole → 4-{[(Imidazole-1-carbonyl)-amino]-methyl}cyclohexanecarboxylic acid methyl ester

HRID 909082

反応式

HRID 909082 の反応式
[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][CH:8]([CH2:11][NH2:12])[CH2:7][CH2:6]1)=[O:4].[C:13](N1C=CN=C1)([N:15]1[CH:19]=[CH:18][N:17]=[CH:16]1)=[O:14]>CN(C)C=O>[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][CH:8]([CH2:11][NH:12][C:13]([N:15]2[CH:19]=[CH:18][N:17]=[CH:16]2)=[O:14])[CH2:7][CH2:6]1)=[O:4]

参加物

4

反応物 2

HCID 682631,1'-CarbonyldiimidazoleHCID 12721444(1R,4R)-Methyl 4-(aminomethyl)cyclohexanecarboxylate

生成物 1

HCID 670955844-{[(Imidazole-1-carbonyl)-amino]-methyl}cyclohexanecarboxylic acid methyl ester収率 93.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a mixture of 4-aminomethyl-cyclohexanecarboxylic acid methyl ester (1.008 g, 4.758 mmol, Astatech,) in N,N-dimethyl formamide (20.0 mL) was added TEA (617 mg, 6.098 mmol) and 1,1′-carbonyldiimidazole (810.3 mg, 4.997 mmol, Aldrich,). After it was stirred at rt for 21 hrs under an argon atmosphere, the solvent was removed and the reaction mixture was extracted with EtOAc, and washed with water (2×), and saturated NaCl. The organic phase was separated, dried over Na2SO4, filtered and concentrated to give 4-{[(imidazole-1-carbonyl)-amino]-methyl}cyclohexanecarboxylic acid methyl ester (1.184 g, 4.46 mmol, 93%) which was used without further purification.

後処理

  1. customthe solvent was removed
  2. extractionthe reaction mixture was extracted with EtOAc
  3. washwashed with water (2×), and saturated NaCl
  4. customThe organic phase was separated
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-20ac29ce42c7452593dadafcd749e935
出典データセット
uspto-grants-2011_09
特許番号
US08017607B2

関連ノート

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