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

HRID 1053604Notes

Reaction equation

HRID 1053604 reaction equation
Cl.C(OC([NH:9][CH2:10][CH2:11][NH:12][C:13]1[CH:14]=[C:15]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([O:27][CH3:28])=[O:26])[CH:20]=2)[CH:16]=[CH:17][CH:18]=1)=O)(C)(C)C>C(OCC)(=O)C>[CH3:28][O:27][C:25]([C:21]1[CH:20]=[C:19]([C:15]2[CH:16]=[CH:17][CH:18]=[C:13]([NH:12][CH2:11][CH2:10][NH2:9])[CH:14]=2)[CH:24]=[CH:23][CH:22]=1)=[O:26]

Participants

4

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 86%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Hydrogen chloride was bubbled through a solution of methyl 3′-(2-(tert-butoxycarbonylamino)ethylamino)biphenyl-3-carboxylate (800 mg, 2.16 mmol, 1.00 equiv.) in ethyl acetate (20 mL), for about 1 hour. The solids were collected by filtration, and then dissolved in saturated solution of sodium bicarbonate (10 mL). After extracting with ethyl acetate (3×100 mL) the organic phases were combined and concentrated to give the title product as a light-yellow oil (500 mg; yield=86%). 1H NMR (300 MHz, DMSO-d6) δ: 8.14 (s, 1H), 7.93 (m, 2H), 7.61 (t, J=7.8 Hz, 1H), 7.27 (t, J=8.1 Hz, 1H), 6.97 (m, 2H), 6.73 (d, J=1.5 Hz, 1H), 3.89 (s, 3H), 3.40 (t, J=6.3 Hz, 2H), 3.01 (m, 2H).

Workup

  1. filtrationThe solids were collected by filtration
  2. dissolutiondissolved in saturated solution of sodium bicarbonate (10 mL)
  3. extractionAfter extracting with ethyl acetate (3×100 mL) the organic phases
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-01398d6c3e7443fa9544760f56724080
Source dataset
uspto-grants-2016_07
Patent number
US09394239B2

Reaction notes

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