1H-imidazole-2-carbaldehyde → HCID 20872881, compound

HRID 497558Notes

Reaction equation

HRID 497558 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12]([CH2:17]P(OC)(OC)=O)[C:13]([O:15][CH3:16])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:24][N:25](C)[C:26](=N)[N:27]([CH3:29])C.N1C=CN=C1C=O>O1CCCC1>[CH2:1]([O:8][C:9]([NH:11]/[C:12](=[CH:17]\[C:26]1[NH:25][CH:24]=[CH:29][N:27]=1)/[C:13]([O:15][CH3:16])=[O:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 249551H-imidazole-2-carbaldehydeHCID 664601,1,3,3-TetramethylguanidineHCID 22319456HCID 22319456, compound

Product 1

HCID 20872881HCID 20872881, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-40 °C

Procedure

A mixture of methyl 2-{[(benzyloxy)carbonyl]amino}-3-(dimethoxyphosphoryl)-propanoate (1 g, 30 mmol) in tetrahydrofuran (7 ml) was stirred at −40° C. and tetramethylguanidine (380 mg, 33 mmol) was added. The reaction mixture was stirred at −40° C. for 20 minutes and then imidazole-2-carboxaldehyde (317 mg, 33 mmol) was added. The reaction was then allowed to warm to room temperature and was stirred at room temperature for 18 h. The solvent was then removed by evaporation under reduced pressure and the residue dissolved in ethyl acetate and washed with water and then brine. The organic phase was then dried (MgSO4), filtered, and then concentrated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with a solvent gradient of ethyl acetate:pentane (30:70 to 80:20), to give the title compound, 366 mg, 40% yield.

Workup

  1. stirringThe reaction mixture was stirred at −40° C. for 20 minutes
  2. temperatureto warm to room temperature
  3. stirringwas stirred at room temperature for 18 h
  4. customThe solvent was then removed by evaporation under reduced pressure
  5. dissolutionthe residue dissolved in ethyl acetate
  6. washwashed with water
  7. dry with materialThe organic phase was then dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by column chromatography on silica gel
  11. washeluting with a solvent gradient of ethyl acetate:pentane (30:70 to 80:20)

Sources & evidence

ORD record
ord-d2219f776a274835b238a63554c380b2
Source dataset
uspto-grants-2005_09
Patent number
US06949577B2

Reaction notes

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