Hydrochloric Acid → Ethyl 3-(6-aminopyridin-3-yl)-2-(1-cyclohexyl-1H-imidazol-4-yl)propionate

HRID 512741Notes

Reaction equation

HRID 512741 reaction equation
[CH2:1]([O:3][C:4](=[O:32])[CH:5]([C:21]1[N:22]=[CH:23][N:24]([CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)[CH:25]=1)[CH2:6][C:7]1[CH:8]=[N:9][C:10]([NH:13]C(OC(C)(C)C)=O)=[CH:11][CH:12]=1)[CH3:2].Cl>C(O)C>[CH2:1]([O:3][C:4](=[O:32])[CH:5]([C:21]1[N:22]=[CH:23][N:24]([CH:26]2[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]2)[CH:25]=1)[CH2:6][C:7]1[CH:8]=[N:9][C:10]([NH2:13])=[CH:11][CH:12]=1)[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 498190113-(6-tert-Butoxycarbonylamino-pyridin-3-yl)-2-(1-cyclohexyl-1H-imidazol-4-yl)-propionic acid ethyl ester

Product 1

HCID 11544682Ethyl 3-(6-aminopyridin-3-yl)-2-(1-cyclohexyl-1H-imidazol-4-yl)propionateYield 99.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

39.0 g (88.1 mmol) 3-(6-tert-Butoxycarbonylamino-pyridin-3-yl)-2-(1-cyclohexyl-1H-imidazol-4-yl)-propionic acid ethyl ester as prepared in process step b) were suspended in 200 ml Ethanol (EtOH) at RT. The mixture was saturated with HCl and was then refluxed for 2 h. The mixture was concentrated and the residue was treated with saturated aqueous K2CO3 (pH 9.0). The aqueous layer was extracted with AcOEt (3×200 ml). The combined organic layers were washed with brine (100 ml), dried with MgSO4 and concentrated to yield the title compound (30 g, 87.6 mmol, 99%) as brown oil.

Workup

  1. temperaturewas then refluxed for 2 h
  2. concentrationThe mixture was concentrated
  3. additionthe residue was treated with saturated aqueous K2CO3 (pH 9.0)
  4. extractionThe aqueous layer was extracted with AcOEt (3×200 ml)
  5. washThe combined organic layers were washed with brine (100 ml)
  6. dry with materialdried with MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-56f2c48d685343918bdced71598000d1
Source dataset
uspto-grants-2015_08
Patent number
US09102657B2

Reaction notes

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