Ethyl 2-{3'-[(tert-butoxycarbonylmethylamino)methyl]biphenyl-4-yloxy}benzoate → HCID 21911081, compound

HRID 1245435Notes

Reaction equation

HRID 1245435 reaction equation
C(OC([CH2:8][NH:9][CH2:10][C:11]1[CH:12]=[C:13]([C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24]3[CH:34]=[CH:33][CH:32]=[CH:31][C:25]=3[C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:19][CH:18]=2)[CH:14]=[CH:15][CH:16]=1)=O)(C)(C)C>ClCCl.FC(F)(F)C(O)=O>[CH3:8][NH:9][CH2:10][C:11]1[CH:12]=[C:13]([C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24]3[CH:34]=[CH:33][CH:32]=[CH:31][C:25]=3[C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:19][CH:18]=2)[CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 1

HCID 21911050Ethyl 2-{3'-[(tert-butoxycarbonylmethylamino)methyl]biphenyl-4-yloxy}benzoate

Product 1

HCID 21911081HCID 21911081, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

3.1 g (6.7 mmol) of ethyl 2-{3′-[(tert-butoxycarbonylmethylamino)-methyl]biphenyl-4-yloxy}benzoate are placed in 50 ml of dichloromethane and 2.6 ml of trifluoroacetic acid. After stirring at room temperature for 8 hours, the reaction medium is concentrated, placed in water, brought to pH 8 with aqueous 1N sodium hydroxide solution and extracted with ethyl acetate. The organic phase is dried over sodium sulfate, filtered and concentrated under vacuum. 2.3 g of ethyl 2-(3′-methylaminomethylbiphenyl-4-yloxy)benzoate are obtained in the form of an orange-colored oil, in a yield of 95%.

Workup

  1. concentrationthe reaction medium is concentrated
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-c10d44c325fc470480183970a10a80f2
Source dataset
uspto-grants-2006_10
Patent number
US07125869B2

Reaction notes

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