Dicyclohexylcarbodiimide → HCID 14877556, compound

HRID 1975601Notes

Reaction equation

HRID 1975601 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH3:24])=[C:5]([C:20]([O:22][CH3:23])=[O:21])[CH:6]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=2)[C:7]=1[C:8]([OH:10])=[O:9].[N:25]1([CH:30]([C:32]2[CH:37]=[CH:36][C:35](/[CH:38]=[CH:39]/[CH2:40]O)=[CH:34][CH:33]=2)[CH3:31])[CH:29]=[CH:28][N:27]=[CH:26]1.C1(N=C=NC2CCCCC2)CCCCC1>C1(C)C=CC=CC=1>[CH3:1][C:2]1[NH:3][C:4]([CH3:24])=[C:5]([C:20]([O:22][CH3:23])=[O:21])[CH:6]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=2)[C:7]=1[C:8]([O:10][CH2:40]/[CH:39]=[CH:38]/[C:35]1[CH:34]=[CH:33][C:32]([CH:30]([N:25]2[CH:29]=[CH:28][N:27]=[CH:26]2)[CH3:31])=[CH:37][CH:36]=1)=[O:9]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 1733222,6-Dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid monomethyl esterHCID 19100056HCID 19100056, compound

Product 1

HCID 14877556HCID 14877556, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

332 mg (1 mM) of 1,4-dihydro-2,6-dimethyl-5-methoxycarbonyl-4-(3-nitrophenyl)pyridine-3-carboxylic acid together with 228 mg (1 mM) of (E)-3-[4{-1-(1-imidazolyl)ethyl)phenyl]-2-propen-1-ol, 248 mg (1.2 mM) of dicyclohexylcarbodiimide and 134 mg (1.1 mM) of 4-N,N-dimethylaminopyridine were dissolved in 5 ml of toluene, while heating, and refluxed for six hours. The solution was cooled to room temperature, and the crystals produced were filtered off. The filtrate was washed with water and dried over anhydrous sodium sulfate. After the solvent was distilled off, the residue was purified by chromatography on a silica gel column, whereby the captioned compound was obtained. The yield was 519 mg (95.7%).

Workup

  1. temperaturewhile heating
  2. temperaturerefluxed for six hours
  3. customthe crystals produced
  4. filtrationwere filtered off
  5. washThe filtrate was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationAfter the solvent was distilled off
  8. customthe residue was purified by chromatography on a silica gel column, whereby the captioned compound
  9. customwas obtained

Sources & evidence

ORD record
ord-c35487c05bef4dcd901683823a269c25
Source dataset
uspto-grants-1994_02
Patent number
US05286869

Reaction notes

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