Diisopropylethylamine → HCID 67067255, compound

HRID 2235721Notes

Reaction equation

HRID 2235721 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-8fa1cfdcec8a4aeda1fc81c353443125
Source dataset
uspto-grants-2010_05
Patent number
US07713993B2

Reaction notes

Loading…