Tetrahydrofuran → HCID 53972102, compound

HRID 368999Notes

Reaction equation

HRID 368999 reaction equation
[C:1]1([CH:7]([CH2:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:8][C:9]([OH:11])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([N:28]1[CH:32]=[CH:31]N=C1)(N1C=CN=C1)=O.C[C:34]1[C:35]([O:44][CH2:45]C)=[C:36](CCN)[CH:37]=[CH:38][C:39]=1C.[O:47]1CCC[CH2:48]1>>[CH3:45][O:44][C:35]1[CH:36]=[C:37]([CH2:31][CH2:32][NH:28][C:9]([CH2:8][CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:11])[CH:38]=[CH:39][C:34]=1[O:47][CH3:48]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 682631,1'-CarbonyldiimidazoleHCID 23284629HCID 23284629, compoundHCID 53867309HCID 53867309, compound

Product 1

HCID 53972102HCID 53972102, compound

Procedure

A solution of 3.0 g (11.8 mmol) of 2,5-diphenylpentane carboxylic acid and 1.91 9 (11.8 mmol) of carbonyldiimidazole is stirred at ambient temperature for one hour and then mixed with a solution of 2.13 g (11.8 mmol) of 2-(3,4-dimethylethoxyphenyl)ethylamine in 20 ml of tetrahydrofuran, stirred overnight at ambient temperature and, after the solvent has been distilled off, the residue is dissolved in ethyl acetate. The organic phase is washed twice with 15 ml of 1N HCl, twice with 20 ml of saturated NaHCO3 solution and then with a saturated NaCl solution. After drying over MgSO4 and distilling off the solvent, 4.9 g (100% of theory) of the desired end product are left, and this end product is further processed in the form of an oil without any more purification.

Workup

  1. distillationafter the solvent has been distilled off
  2. dissolutionthe residue is dissolved in ethyl acetate
  3. washThe organic phase is washed twice with 15 ml of 1N HCl, twice with 20 ml of saturated NaHCO3 solution
  4. dry with materialAfter drying over MgSO4
  5. distillationdistilling off the solvent, 4.9 g (100% of theory) of the desired end product
  6. waitare left
  7. customthis end product is further processed in the form of an oil without any more purification

Sources & evidence

ORD record
ord-be4a94ff7a074ec3b50b59fe8168cdd2
Source dataset
uspto-grants-2000_10
Patent number
US06136819

Reaction notes

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