Hydrochloric Acid → 3'-(2-Amino-ethylamino)-biphenyl-3-carboxylic acid methyl ester

HRID 1069086Notes

Reaction equation

HRID 1069086 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([NH:17][CH2:18][CH2:19][NH:20]C(OC(C)(C)C)=O)[CH:12]=2)[CH:8]=[CH:9][CH:10]=1)=[O:4].Cl>O1CCOCC1.CCOCC>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([NH:17][CH2:18][CH2:19][NH2:20])[CH:12]=2)[CH:8]=[CH:9][CH:10]=1)=[O:4]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 21191174Methyl 3'-(2-(tert-butoxycarbonylamino)ethylamino)biphenyl-3-carboxylate

Product 1

HCID 211911673'-(2-Amino-ethylamino)-biphenyl-3-carboxylic acid methyl esterYield 22%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

To methyl-3′-[(2-[[(tert-butoxy)carbonyl]amino]ethyl)amino]-[1,1′-biphenyl]-3-carboxylate (730 mg) was added 4 N HCl in dioxane (20 mL) and the mixture was stirred under nitrogen for 16 h. The white mixture was diluted with ether, and the dihydrochloride salt of the title compound was collected as a white solid (566 mg) by suction filtration. A portion of this material (128 mg) was partitioned between saturated aqueous sodium bicarbonate (30 mL) and ethyl acetate (30 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated to give the title compound (117 mg) as a colorless oil. Electrospray MS (positive ion): (M+H) 272

Workup

  1. filtrationthe dihydrochloride salt of the title compound was collected as a white solid (566 mg) by suction filtration
  2. customA portion of this material (128 mg) was partitioned between saturated aqueous sodium bicarbonate (30 mL) and ethyl acetate (30 mL)
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-10c5bb44a7a4457c823b4b219dcf93c0
Source dataset
uspto-grants-2001_06
Patent number
US06251925B1

Reaction notes

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