Hydrochloric Acid → Methyl 4'-[2-(benzylamino)ethyl]-3-(isopropylamino)-4-biphenylcarboxylate

HRID 2220371Notes

Reaction equation

HRID 2220371 reaction equation
[CH2:1]([N:8](C(OC(C)(C)C)=O)[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([O:25][CH3:26])=[O:24])=[C:19]([NH:27][CH:28]([CH3:30])[CH3:29])[CH:18]=2)=[CH:13][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>O1CCCC1.O1CCOCC1>[CH2:1]([NH:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([O:25][CH3:26])=[O:24])=[C:19]([NH:27][CH:28]([CH3:30])[CH3:29])[CH:18]=2)=[CH:13][CH:12]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 69102971Methyl 4'-[2-[benzyl(tert-butoxycarbonyl)amino)ethyl]-3-(isopropylamino)-4-biphenylcarboxylate

Product 1

HCID 69103631Methyl 4'-[2-(benzylamino)ethyl]-3-(isopropylamino)-4-biphenylcarboxylateYield 97.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of methyl 4′-[2-[benzyl(tert-butoxycarbonyl)amino)ethyl]-3-(isopropylamino)-4-biphenylcarboxylate (768 mg) in tetrahydrofuran (8 ml) was added 4N hydrogen chloride solution in 1,4-dioxane (8 ml) at 0° C., and the mixture was stirred at room temperature overnight. The mixture was evaporated under reduced pressure and the residue was diluted with chloroform and water. The mixture was basified with aqueous solution of sodium hydroxide (1N) and the organic layer was separated, dried over magnesium sulfate and evaporated under reduced pressure to give methyl 4′-[2-(benzylamino)ethyl]-3-(isopropylamino)-4-biphenylcarboxylate (600 mg).

Workup

  1. customThe mixture was evaporated under reduced pressure
  2. additionthe residue was diluted with chloroform and water
  3. customthe organic layer was separated
  4. dry with materialdried over magnesium sulfate
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-6c97fc5bddf44f6ea3b45f28605b07f9
Source dataset
uspto-grants-2008_08
Patent number
US07417060B2

Reaction notes

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