Hydrochloric Acid → HCID 28873201, compound

HRID 1046467Notes

Reaction equation

HRID 1046467 reaction equation
N[C@H](C(O)=O)CC1N=CNC=1.[OH-].[Na+].C(=O)C(C)C.Cl.[CH:20]([CH:23]1[C:28]2[N:29]=[CH:30][NH:31][C:27]=2[CH2:26][CH:25]([C:32]([OH:34])=[O:33])[NH:24]1)([CH3:22])[CH3:21]>O.CO>[CH:20]([C@H:23]1[C:28]2[N:29]=[CH:30][NH:31][C:27]=2[CH2:26][C@@H:25]([C:32]([OH:34])=[O:33])[NH:24]1)([CH3:22])[CH3:21]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6561IsobutyraldehydeHCID 14798Sodium HydroxideHCID 17112375HCID 17112375, compoundHCID 178419078HCID 178419078, compound

Product 1

HCID 28873201HCID 28873201, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

L-Histidine (10.0 g, 43.8 mmol) was dissolved in a solution of NaOH (7.73 g, 193 mmol) in water (25 mL) and MeOH (100 mL), and isobutyraldehyde (11.8 mL, 129 mmol) was added. The reaction mixture was heated under reflux at 80° C. for 24 h. The pH was adjusted to 7 with 1 M aq HCl solution and the solvents were removed in vacuo. The residue was dissolved in hot EtOH and cooled to room temperature. The precipitate was removed by filtration and the mother liquor concentrated in vacuo, washed with acetone (100 mL) and dried to give 4-isopropyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylic acid as a pale yellow solid (18.6 g, crude, 6:1 mixture of (4S,6S):(4R,6S) diastereoisomers).

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was heated
  3. customthe solvents were removed in vacuo
  4. dissolutionThe residue was dissolved in hot EtOH
  5. temperaturecooled to room temperature
  6. customThe precipitate was removed by filtration
  7. concentrationthe mother liquor concentrated in vacuo
  8. washwashed with acetone (100 mL)
  9. customdried
  10. customto give

Sources & evidence

ORD record
ord-094d4d142cf549eb89d1cef3f781bb3c
Source dataset
uspto-grants-2013_10
Patent number
US08569338B2

Reaction notes

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