Imidazole → HCID 45092100, compound

HRID 899732Notes

Reaction equation

HRID 899732 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Na+].[C:8]([O:12][C:13]([NH:15][CH2:16][CH2:17]OS(C1C=CC(C)=CC=1)(=O)=O)=[O:14])([CH3:11])([CH3:10])[CH3:9]>CN(C=O)C>[C:8]([O:12][C:13](=[O:14])[NH:15][CH2:16][CH2:17][N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1)([CH3:11])([CH3:10])[CH3:9]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 10781634tert-butyl N-{2-[(4-methylbenzenesulfonyl)oxy]ethyl}carbamate

Product 1

HCID 45092100HCID 45092100, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of imidazole (253 mg, 3.72 mmol) in DMF (2 mL) was added to a suspension of NaH (60% in mineral oil, 164 mg, 4.10 mmol) in DMF (8 mL), and the mixture was stirred at room temperature for 45 minutes. A solution of toluene-4-sulfonic acid 2-tert-butoxycarbonylamino-ethyl ester (1.29 g, 4.09 mmol) in DMF (6 mL) was added, and the mixture was stirred at room temperature for 16 h then concentrated in vacuo. The residue was partitioned between H2O (25 mL) and EtOAc (25 mL), and the aqueous phase was extracted with EtOAc (25 mL). The combined organic phases were dried (MgSO4) and concentrated in vacuo. Purification of the crude material by column chromatography on silica gel (200:5:1-100:5:1 CH2Cl2/MeOH/NH4OH) gave a colourless oil (224 mg, 29%). 1H NMR (CDCl3) δ 1.44 (s, 9H), 3.43 (m, 2H), 4.08 (m, 2H), 4.64 (br s, 1H), 6.92 (s, 1H), 7.09 (s, 1H), 7.46 (s, 1H).

Workup

  1. stirringthe mixture was stirred at room temperature for 16 h
  2. concentrationthen concentrated in vacuo
  3. customThe residue was partitioned between H2O (25 mL) and EtOAc (25 mL)
  4. extractionthe aqueous phase was extracted with EtOAc (25 mL)
  5. dry with materialThe combined organic phases were dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customPurification of the crude material by column chromatography on silica gel (200:5:1-100:5:1 CH2Cl2/MeOH/NH4OH)

Sources & evidence

ORD record
ord-010df403104c4bd3857b8b96b5283718
Source dataset
uspto-grants-2008_04
Patent number
US07354934B2

Reaction notes

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