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

HRID 560069노트

반응식

HRID 560069 반응식
[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

참가 물질

6

반응물 3

HCID 15891Phenyl chloroformateHCID 516892Sodium BicarbonateHCID 178419023HCID 178419023, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매2회HCID 8028Tetrahydrofuran용매

실험 절차

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-Hexahydropentalen-1-ylmethyl)-1,3-dihydro-imidazol-2-one (Compound 41).

후처리

  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

출처 및 근거

ORD 기록
ord-6f3933ace80642ae9393dfcdf4fea919
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063087B2

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