Diisopropylethylamine → HCID 66895016, compound

HRID 19237Notes

Reaction equation

HRID 19237 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C@@H:4]([NH2:12])[CH2:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.C(N(CC)C(C)C)(C)C.C([O:25][C:26](=O)/[CH:27]=[C:28](/[O:31][C:32]1[CH:37]=[C:36]([Cl:38])[CH:35]=[CH:34][C:33]=1[Cl:39])\[CH2:29]Br)C>CN(C)C=O>[CH3:1][O:2][C:3](=[O:13])[C@@H:4]([N:12]1[CH2:29][C:28]([O:31][C:32]2[CH:37]=[C:36]([Cl:38])[CH:35]=[CH:34][C:33]=2[Cl:39])=[CH:27][C:26]1=[O:25])[CH2:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 13833920Methyl 3-cyclohexyl-L-alaninateHCID 66894821HCID 66894821, compound

Product 1

HCID 66895016HCID 66895016, compoundYield 15.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of (S)-2-amino-3-cyclohexyl-propionic acid methyl ester (750 mg, 0.004 mol) in N,N-dimethylformamide (10 mL) was added N,N-diisopropylethylamine (2.6 g, 0.02 mol) slowly at room temperature, under nitrogen. The resulting mixture was stirred for 5 min and then treated with (E)-4-bromo-3-(2,5-dichloro-phenoxy)-but-2-enoic acid ethyl ester (1.5 g, 0.004 mol) and the reaction mixture was heated at 110° C.-120° C. for 16 h. After this time, ice water was added and the resulting mixture was extracted with ethyl acetate. The combined organic layers were washed with a saturated aqueous sodium chloride solution, dried over sodium sulfate and concentrated in vacuo. Purification by flash column chromatography (silica gel (100-200 mesh)) afforded (S)-3-cyclohexyl-2-[4-(2,5-dichloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-propionic acid methyl ester (250 mg, 15%) as yellow oil.

Workup

  1. temperaturethe reaction mixture was heated at 110° C.-120° C. for 16 h
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. washThe combined organic layers were washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customPurification by flash column chromatography (silica gel (100-200 mesh))

Sources & evidence

ORD record
ord-759a56c5ccc54e19b7dfec9c989cc7fe
Source dataset
uspto-grants-2010_06
Patent number
US07741327B2

Reaction notes

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