Phenyl chloroformate → 4-(1,2,3,4,5,6-Hexahydropentalen-1-ylmethyl)-1,3-dihydro-imidazol-2-one

HRID 28751ノート

反応式

HRID 28751 の反応式
[CH:1]1([CH2:9][C:10]2[N:11]=[CH:12][NH:13][CH:14]=2)[C:8]2[CH2:7][CH2:6][CH2:5][C:4]=2[CH2:3][CH2:2]1.C([O-])(O)=[O:16].[Na+].ClC(OC1C=CC=CC=1)=O>C1COCC1.O>[CH:1]1([CH2:9][C:10]2[NH:11][C:12](=[O:16])[NH:13][CH:14]=2)[C:8]2[CH2:7][CH2:6][CH2:5][C:4]=2[CH2:3][CH2:2]1

参加物

6

反応物 3

HCID 15891Phenyl chloroformateHCID 516892Sodium BicarbonateHCID 178419023HCID 178419023、化合物

生成物 1

HCID 219861944-(1,2,3,4,5,6-Hexahydropentalen-1-ylmethyl)-1,3-dihydro-imidazol-2-one

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 4-(1,2,3,4,5,6-hexahydro-pentalen-1-ylmethyl)-1H-imidazole; fumarate salt (Intermediate A5 as described in Example A, 340 mg, 1.81 mmol) in THF (15 mL) and water (15 mL) was treated with NaHCO3 (1.52 g, 18 mmol) at rt for 30 m. Phenyl chloroformate (600 mL, 4.7 mmol) was added and stirring was continued for 1 h at 65° C. The mixture was diluted with water (30 mL) and extracted with EtOAc (3×30 mL). The organic portions were combined and freed of solvent. The residue was dissolved in EtOH (15 mL):water (15 mL) and treated with Na2CO3 (500 mg) for 1.5 h at 95° C. The mixture was cooled to rt and the product was collected on a glass frit to give a white solid (˜50%) 4-(1,2,3,4,5,6-Hexahydro-pentalen-1-ylmethyl)-1,3-dihydro-imidazol-2-one (Compound 41).

後処理

  1. extractionextracted with EtOAc (3×30 mL)
  2. dissolutionThe residue was dissolved in EtOH (15 mL)
  3. additionwater (15 mL) and treated with Na2CO3 (500 mg) for 1.5 h at 95° C
  4. customthe product was collected on a glass frit

出典と根拠

ORDレコード
ord-c21dc13d27ca4922994f66a1bc4cc4be
出典データセット
uspto-grants-2008_09
特許番号
US07419994B2

反応ノート

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