Diisopropylethylamine → HCID 67067255, compound

HRID 1009380Notes

Reaction equation

HRID 1009380 reaction equation
C(N(C(C)C)CC)(C)C.C1N(P(Cl)(N2C(=O)OCC2)=O)C(=O)OC1.Cl.[Cl:26][CH2:27][CH2:28][CH2:29][CH:30]([C:35]1[C:40]([F:41])=[CH:39][C:38]([F:42])=[CH:37][C:36]=1[F:43])[C:31]([NH:33][NH2:34])=[O:32].[CH3:44][O:45][C:46]1[CH:47]=[C:48](/[CH:58]=[CH:59]/[C:60](O)=[O:61])[CH:49]=[CH:50][C:51]=1[N:52]1[CH:56]=[C:55]([CH3:57])[N:54]=[CH:53]1.O.C(=O)(O)[O-].[Na+]>C(Cl)Cl.C(OCC)(=O)C>[CH3:44][O:45][C:46]1[CH:47]=[C:48](/[CH:58]=[CH:59]/[C:60]([NH:34][NH:33][C:31](=[O:32])[CH:30]([C:35]2[C:36]([F:43])=[CH:37][C:38]([F:42])=[CH:39][C:40]=2[F:41])[CH2:29][CH2:28][CH2:27][Cl:26])=[O:61])[CH:49]=[CH:50][C:51]=1[N:52]1[CH:56]=[C:55]([CH3:57])[N:54]=[CH:53]1

Participants

8

Reactant 5

HCID 81531DiisopropylethylamineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 59528030(E)-3-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]acrylic acidHCID 67067275HCID 67067275, compoundHCID 86585896Sodium bicarbonate water

Product 1

HCID 67067255HCID 67067255, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

IPEA (0.46 mL) and BOPCl (333 mg) were added to a solution of 5-chloro-2-(2,4,6-trifluorophenyl)pentanoic acid hydrazide hydrochloride (277 mg) and (E)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]acrylic acid (225 mg) in methylene chloride (10 mL), and the reaction solution was stirred at room temperature for two hours. Ethyl acetate and saturated sodium bicarbonate water were added to the reaction solution, and the organic layer was separated. The resulting organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane:ethyl acetate=1:1->ethyl acetate->ethyl acetate:methanol=9:1) to obtain 286 mg of the title compound. The property value of the compound is as follows.

Workup

  1. customthe organic layer was separated
  2. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (elution solvent: heptane:ethyl acetate=1:1->ethyl acetate->ethyl acetate:methanol=9:1)

Sources & evidence

ORD record
ord-a07d0930eded404f88cbfad54f55dd34
Source dataset
uspto-grants-2011_07
Patent number
US07973033B2

Reaction notes

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