HCID 86664896, compound → HCID 178472509, compound

HRID 1183198Notes

Reaction equation

HRID 1183198 reaction equation
C([N:20]1[CH:24]=[C:23]([C:25]2[CH:30]=[CH:29][C:28]([C@H:31]3[CH2:33][C@@H:32]3[C:34]([O:36][CH2:37][CH3:38])=[O:35])=[CH:27][CH:26]=2)[N:22]=[CH:21]1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>CO.Cl>[NH:20]1[CH:24]=[C:23]([C:25]2[CH:26]=[CH:27][C:28]([C@H:31]3[CH2:33][C@@H:32]3[C:34]([O:36][CH2:37][CH3:38])=[O:35])=[CH:29][CH:30]=2)[N:22]=[CH:21]1

Participants

4

Reactant 1

HCID 86664896HCID 86664896, compound

Product 1

HCID 178472509HCID 178472509, compoundYield 66.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

Ethyl (1S,2S)-2-[4-(1-trityl-1H-imidazol-4-yl)phenyl]cyclopropanecarboxylate (4.1 g, from Step 1) was suspended in 30 mL of methanol and 30 mL of 1N HCl. The reaction mixture was heated at reflux for 2 hours. The solvent was evaporated in vacuo and the residue was triturated with ether (100 mL). The liquid organic layer was discarded. The solid was the desired product HCl salt. To the solid were added 100 mL EtOAc and 13 mL of 1N NaOH to release the free base. The aqueous/organic mixture was shaken in a separation funnel. The aqueous layer was discarded, and the organic layer was washed with brine, dried with MgSO4, filtered, and concentrated in vacuo to give the title compound (1.4 g, 66.4%). 1H NMR (500 MHz, (CD3OD): 7.98 (s, 1H), 7.58 (d, 2H), 7.39 (s, 1H), 7.17 (d, 2H), 4.18 (q, 2H), 2.43 (m, 1H), 1.86 (m, 1H), 1.57 (m, 1H), 1.37 (m, 1H), 1.24 (t, 3H). LCMS: ink 257 (M+H)+.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 2 hours
  3. customThe solvent was evaporated in vacuo
  4. customthe residue was triturated with ether (100 mL)
  5. additionTo the solid were added 100 mL EtOAc and 13 mL of 1N NaOH
  6. washthe organic layer was washed with brine
  7. dry with materialdried with MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-01782048a71b43b7b7028f3f89e62685
Source dataset
uspto-grants-2014_03
Patent number
US08664253B2

Reaction notes

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