Diisopropylethylamine → HCID 66839205, compound

HRID 546733Notes

Reaction equation

HRID 546733 reaction equation
C(N(C(C)C)CC)(C)C.[CH3:10][O:11][C:12]1[CH:13]=[C:14](/[CH:24]=[CH:25]/[C:26]([OH:28])=O)[CH:15]=[CH:16][C:17]=1[N:18]1[CH:22]=[C:21]([CH3:23])[N:20]=[CH:19]1.C1N(P([Cl:43])(N2C(=O)OCC2)=O)C(=O)OC1.O[CH2:45][CH2:46][CH:47]([C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1)[CH2:48][C:49]([NH:51][NH2:52])=O>C(Cl)Cl.O>[Cl:43][CH2:45][CH2:46][CH:47]([C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1)[CH2:48][C:49]1[O:28][C:26](/[CH:25]=[CH:24]/[C:14]2[CH:15]=[CH:16][C:17]([N:18]3[CH:22]=[C:21]([CH3:23])[N:20]=[CH:19]3)=[C:12]([O:11][CH3:10])[CH:13]=2)=[N:52][N:51]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 59528030(E)-3-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]acrylic acidHCID 66839680HCID 66839680, compound

Product 1

HCID 66839205HCID 66839205, compoundYield 42.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

IPEA (2.0 mL), (E)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]acrylic acid (600 mg) and BOPCl (0.71 g) were added to a solution of 5-hydroxy-3-phenylpentanoic acid hydrazide (492 mg) in methylene chloride (20 mL) at room temperature, and the reaction solution was stirred at room temperature for seven hours. Water was added to the reaction solution, followed by extraction with chloroform. The resulting extract was washed with a saturated sodium bicarbonate solution. The resulting organic layer was dried over magnesium sulfate and then concentrated under reduced pressure. Phosphorus oxychloride (10 mL) was added to the resulting residue at room temperature, and the reaction solution was heated under reflux for 1.5 hours. The reaction solution was left to cool to room temperature and then concentrated under reduced pressure. A saturated sodium bicarbonate solution was added to the residue, followed by extraction with ethyl acetate. The resulting extract was dried over magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (carrier: Chromatorex NH; elution solvent: heptane-ethyl acetate system) to obtain 445 mg of the title compound. The property value of the compound is as follows.

Workup

  1. extractionfollowed by extraction with chloroform
  2. extractionThe resulting extract
  3. washwas washed with a saturated sodium bicarbonate solution
  4. dry with materialThe resulting organic layer was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. additionPhosphorus oxychloride (10 mL) was added to the resulting residue at room temperature
  7. temperaturethe reaction solution was heated
  8. temperatureunder reflux for 1.5 hours
  9. waitThe reaction solution was left
  10. temperatureto cool to room temperature
  11. concentrationconcentrated under reduced pressure
  12. additionA saturated sodium bicarbonate solution was added to the residue
  13. extractionfollowed by extraction with ethyl acetate
  14. extractionThe resulting extract
  15. dry with materialwas dried over magnesium sulfate
  16. concentrationconcentrated under reduced pressure
  17. customThe residue was purified by silica gel column chromatography (carrier: Chromatorex NH; elution solvent: heptane-ethyl acetate system)

Sources & evidence

ORD record
ord-a396c7f2c8564eea8734624bd74ac2be
Source dataset
uspto-grants-2011_05
Patent number
US07935815B2

Reaction notes

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