Dicyclohexylcarbodiimide → HCID 23056347, compound

HRID 1975600Notes

Reaction equation

HRID 1975600 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].[NH:25]1[CH:29]=[CH:28][N:27]=[C:26]1[CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1/[CH:37]=[CH:38]/[CH2:39]O.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][CH2:39]/[CH:38]=[CH:37]/[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=1[CH2:30][C:26]1[NH:27][CH:28]=[CH:29][N:25]=1)=[O:9]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 1733222,6-Dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid monomethyl esterHCID 86747588HCID 86747588, compound

Product 1

HCID 23056347HCID 23056347, 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 215 mg (1 mM) of (E)-3-{2-(1-imidazolylmethyl)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 away, the residue was purified by chromatography on a silica gel column, whereby the captioned compound was obtained. The yield was 528 mg (100%).

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 away
  8. customthe residue was purified by chromatography on a silica gel column, whereby the captioned compound
  9. customwas obtained

Sources & evidence

ORD record
ord-b514056472894eb9bd72088bbee6ffba
Source dataset
uspto-grants-1994_02
Patent number
US05286869

Reaction notes

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