2-Benzoyloxymethyl-5-[(6,2'-dimethyl-4'-propionylbiphenyl-3-ylamino)methyl]benzyl benzoate → 1-{5'-[3,4-Bis(hydroxymethyl)benzylamino]-2,2'-dimethylbiphenyl-4-yl}-1-propanone

HRID 584326Notes

Reaction equation

HRID 584326 reaction equation
C([O:9][CH2:10][C:11]1[CH:16]=[C:15]([CH2:17][NH:18][C:19]2[CH:20]=[C:21]([C:26]3[CH:31]=[CH:30][C:29]([C:32](=[O:35])[CH2:33][CH3:34])=[CH:28][C:27]=3[CH3:36])[C:22]([CH3:25])=[CH:23][CH:24]=2)[CH:14]=[CH:13][C:12]=1[CH2:37][O:38]C(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(=O)([O-])[O-].[K+].[K+]>[OH:9][CH2:10][C:11]1[CH:16]=[C:15]([CH:14]=[CH:13][C:12]=1[CH2:37][OH:38])[CH2:17][NH:18][C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[C:21]([C:26]2[CH:31]=[CH:30][C:29]([C:32](=[O:35])[CH2:33][CH3:34])=[CH:28][C:27]=2[CH3:36])[CH:20]=1

Participants

3

Reactant 1

HCID 697926032-Benzoyloxymethyl-5-[(6,2'-dimethyl-4'-propionylbiphenyl-3-ylamino)methyl]benzyl benzoate

Product 1

HCID 223456351-{5'-[3,4-Bis(hydroxymethyl)benzylamino]-2,2'-dimethylbiphenyl-4-yl}-1-propanone

Reagents, catalysts & solvents 1

HCID 11430Potassium CarbonateSolvent

Procedure

800 mg (1.3 mmol) of 2-benzoyloxymethyl-5-[(6,2′-dimethyl-4′-propionylbiphenyl-3-ylamino)methyl]benzyl benzoate are dissolved in methanolic 2% potassium carbonate solution and the medium is stirred for 1 hour. After water/dichloromethane extraction, the residue obtained is purified by chromatography on silica gel (eluent: 30 heptane/70 ethyl acetate). A yellow oil is obtained (m=470 mg, Y=88%).

Workup

  1. extractionAfter water/dichloromethane extraction
  2. customthe residue obtained
  3. customis purified by chromatography on silica gel (eluent: 30 heptane/70 ethyl acetate)
  4. customA yellow oil is obtained (m=470 mg, Y=88%)

Sources & evidence

ORD record
ord-67cb5d19725e4edebb65be7a2ad3af0d
Source dataset
uspto-grants-2005_08
Patent number
US06924400B2

Reaction notes

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