1,1'-Carbonyldiimidazole → HCID 68687724, compound

HRID 2245341Notes

Reaction equation

HRID 2245341 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][C:9]([OH:11])=O)[CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.CCN(C(C)C)C(C)C.[CH2:33]([O:35][C:36](=[O:48])[CH2:37][CH2:38][NH:39][CH2:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[CH3:34]>C1COCC1>[CH2:33]([O:35][C:36](=[O:48])[CH2:37][CH2:38][N:39]([C:9](=[O:11])[CH2:8][C:4]1[CH:3]=[C:2]([CH3:1])[CH:7]=[CH:6][N:5]=1)[CH2:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[CH3:34]

Participants

6

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 19380987(4-Methylpyridin-2-yl)acetic acidHCID 19937606HCID 19937606, compound

Product 1

HCID 68687724HCID 68687724, compoundYield 32.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(4-Methyl-pyridin-2-yl)-acetic acid (1.0 g), carbonyldiimidazole (CDI, 1.07 g) and DIPEA (0.856 g) were added to THF (15 ml) and the light brown suspension was allowed to stir at RT for 1 hour. To the mixture was added 3-phenethylamino-propionic acid ethyl ester (0.898 g) dropwise and the resulting mixture was stirred at 55° over night. The mixture was poured into ice/water and the pH was adjusted to 5.0. The mixture was extracted with ethyl acetate and the organic layer was separated, washed with brine, dried over Na2SO4, filtered and evaporated. The residue was purified by flash chromatography (ethyl acetate/hexanes 2:1) to give the desired product as a light brown liquid (0.462 g). MS (ESI): 355.0 (MH+).

Workup

  1. stirringthe resulting mixture was stirred at 55° over night
  2. extractionThe mixture was extracted with ethyl acetate
  3. customthe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by flash chromatography (ethyl acetate/hexanes 2:1)

Sources & evidence

ORD record
ord-08250799ce924bff8e0d906199598943
Source dataset
uspto-grants-2010_03
Patent number
US07683079B2

Reaction notes

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