Dicyclohexylcarbodiimide → Isopropyl (E)-3-[4-(1-imidazolylmethyl)phenyl]-2-propen-1-yl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate

HRID 1975606Notes

Reaction equation

HRID 1975606 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH3:26])=[C:5]([C:20]([O:22][CH:23]([CH3:25])[CH3:24])=[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:27]1[CH:31]=[CH:30][N:29]=[C:28]1[CH2:32][C:33]1[CH:38]=[CH:37][C:36](/[CH:39]=[CH:40]/[CH2:41]O)=[CH:35][CH:34]=1.C1(N=C=NC2CCCCC2)CCCCC1>C1(C)C=CC=CC=1>[CH3:26][C:4]1[NH:3][C:2]([CH3:1])=[C:7]([C:8]([O:10][CH2:41]/[CH:40]=[CH:39]/[C:36]2[CH:35]=[CH:34][C:33]([CH2:32][C:28]3[NH:29][CH:30]=[CH:31][N:27]=3)=[CH:38][CH:37]=2)=[O:9])[CH:6]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=2)[C:5]=1[C:20]([O:22][CH:23]([CH3:24])[CH3:25])=[O:21]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 100214112,6-Dimethyl-4-(3-nitrophenyl)-5-[(propan-2-yloxy)carbonyl]-1,4-dihydropyridine-3-carboxylic acidHCID 21648924(E)-3-[4-(1-imidazolylmethyl)phenyl]-2-propen-1-ol

Product 1

HCID 86747593Isopropyl (E)-3-[4-(1-imidazolylmethyl)phenyl]-2-propen-1-yl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

360 mg (1 mM) of 1,4-dihydro-2,6-dimethyl-5-isopropyloxycarbonyl-4-(3- nitrophenyl)pyridine -3carboxylic acid together with 215 mg (1 mM) of (E)-3-{4-(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 541 mg (97.2%).

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-2edeee193c0b48efa5ae2a3c897b8391
Source dataset
uspto-grants-1994_02
Patent number
US05286869

Reaction notes

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