Dichloromethane → 4-{[(4-Carboxybutyl)(2-{5-fluoro-2-[(4'-methyl-1,1'-biphenyl-4-yl)-methoxy]phenyl}ethyl)amino]methyl}benzoic acid

HRID 8137Notes

Reaction equation

HRID 8137 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][C:35]([C:38]3[CH:43]=[CH:42][C:41]([CH3:44])=[CH:40][CH:39]=3)=[CH:34][CH:33]=2)=[C:6]([CH2:8][CH2:9][N:10]([CH2:19][C:20]2[CH:29]=[CH:28][C:23]([C:24]([O:26]C)=[O:25])=[CH:22][CH:21]=2)[CH2:11][CH2:12][CH2:13][CH2:14][C:15]([O:17]C)=[O:16])[CH:7]=1.[OH-].[Na+].ClCCl>CO>[C:15]([CH2:14][CH2:13][CH2:12][CH2:11][N:10]([CH2:19][C:20]1[CH:29]=[CH:28][C:23]([C:24]([OH:26])=[O:25])=[CH:22][CH:21]=1)[CH2:9][CH2:8][C:6]1[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=1[O:30][CH2:31][C:32]1[CH:37]=[CH:36][C:35]([C:38]2[CH:43]=[CH:42][C:41]([CH3:44])=[CH:40][CH:39]=2)=[CH:34][CH:33]=1)([OH:17])=[O:16]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 22015042Methyl 4-{[(2-{5-fluoro-2-[(4'-methyl-1,1'-biphenyl-4-yl)methoxy]phenyl}ethyl)(5-methoxy-5-oxopentyl)amino]methyl}benzoate

Product 1

HCID 220150444-{[(4-Carboxybutyl)(2-{5-fluoro-2-[(4'-methyl-1,1'-biphenyl-4-yl)-methoxy]phenyl}ethyl)amino]methyl}benzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.45 g (0.69 mmol) of methyl 4-{[(2-{5-fluoro-2-[(4′-methyl-1,1′-biphenyl-4-yl)methoxy]phenyl}ethyl)(5-methoxy-5-oxopentyl)amino]methyl}benzoate from Ex. 185 is dissolved in 8ml of methanol. 0.5 ml of aqueous sodium hydroxide solution (45%) and 1.5 ml of dichloromethane are added, and the solution is stirred at RT for 8 hours. The reaction is extracted with diethyl ether, the aqueous phase is acidified using sulphuric acid and extracted with ethyl acetate and the extract is filtered through Extrelut and concentrated.

Workup

  1. extractionThe reaction is extracted with diethyl ether
  2. extractionextracted with ethyl acetate
  3. filtrationthe extract is filtered through Extrelut
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-501d7d3e9d7d4a4780d07b70281abad3
Source dataset
uspto-grants-2006_08
Patent number
US07087644B1

Reaction notes

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