Trifluoroacetic acid → HCID 19607921, compound

HRID 1603143Notes

Reaction equation

HRID 1603143 reaction equation
[CH3:1][N:2]([CH:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]([C:18](=[O:35])[C:19]2[CH:24]=[CH:23][C:22]([NH:25][C:26](=[O:34])[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[CH3:33])=[CH:21][CH:20]=2)[CH2:10][CH2:9][CH2:8]1)[CH2:3][CH:4]1[CH2:6][O:5]1.FC(F)(F)C(O)=[O:39].C(=O)([O-])[O-].[Na+].[Na+]>>[CH3:1][N:2]([CH:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]([C:18](=[O:35])[C:19]2[CH:20]=[CH:21][C:22]([NH:25][C:26](=[O:34])[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[CH3:33])=[CH:23][CH:24]=2)[CH2:10][CH2:9][CH2:8]1)[CH2:3][CH:4]([OH:39])[CH2:6][OH:5]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 19607968HCID 19607968, compound

Product 1

HCID 19607921HCID 19607921, compound

Procedure

To 5-(N-methyl-N-oxiranylmethylamino)-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.62 g) is added trifluoroacetic acid (1.22 ml) under ice-cooling and the mixture is stirred for 4 hours. The reaction solution is neutralized with aqueous sodium carbonate solution, and extracted three times with dichloromethane. The extract is washed with saturated saline solution and dried over magnesium sulfate. The solvent is distilled off and the resulting residue is dissolved in methanol (10 ml). Thereto is added 40% aqueous sodium hydroxide solution (10 ml) and water (10 ml), and the mixture is stirred at room temperature overnight. Methanol is distilled off and the resulting residue is purified by silica gel column chromatography (eluent; dichloromethane:methanol=30:1) to give 5-[N-methyl-N-(2,3-dihydroxypropyl)amino)-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.23 g) as colorless amorphous.

Workup

  1. temperaturecooling
  2. extractionextracted three times with dichloromethane
  3. washThe extract is washed with saturated saline solution
  4. dry with materialdried over magnesium sulfate
  5. distillationThe solvent is distilled off
  6. dissolutionthe resulting residue is dissolved in methanol (10 ml)
  7. additionThereto is added 40% aqueous sodium hydroxide solution (10 ml) and water (10 ml)
  8. stirringthe mixture is stirred at room temperature overnight
  9. distillationMethanol is distilled off
  10. customthe resulting residue is purified by silica gel column chromatography (eluent; dichloromethane:methanol=30:1)

Sources & evidence

ORD record
ord-519c70c2e1354fdd90bd4838b11414d4
Source dataset
uspto-grants-1999_11
Patent number
US05985869

Reaction notes

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