Dicyclohexylcarbodiimide → HCID 18650845, compound

HRID 1589768Notes

Reaction equation

HRID 1589768 reaction equation
[CH2:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:24]=[CH:23][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=2)=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[Cl:25][C@@H:26]([CH3:38])[CH2:27][C@H:28]([CH3:37])[O:29][C:30]1[CH:35]=[CH:34][C:33](O)=[CH:32][CH:31]=1.N1(C2C=CN=CC=2)CCCC1.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[Cl:25][C@@H:26]([CH3:38])[CH2:27][C@H:28]([CH3:37])[O:29][C:30]1[CH:35]=[CH:34][C:33]([O:21][C:20](=[O:22])[C:19]2[CH:23]=[CH:24][C:16]([C:13]3[CH:14]=[CH:15][C:10]([O:9][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[CH:11][CH:12]=3)=[CH:17][CH:18]=2)=[CH:32][CH:31]=1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 755674-PyrrolidinopyridineHCID 28025564'-(Octyloxy)-[1,1'-biphenyl]-4-carboxylic acidHCID 18650836HCID 18650836, compound

Product 1

HCID 18650845HCID 18650845, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.36 g of 4-(4'-n-octyloxyphenyl)benzoic acid, 0.21 g of (S,S)-4-(3'-chloro-1'-methylbutoxy)phenol, 0.02 g of 4-pyrrolidinopyridine, 0.21 g of dicyclohexylcarbodiimide and 10 ml of methylene chloride were stirred together at room temperature for four hours. The dicyclohexyl urea thus precipitated was filtered and the filtrate was desolvated. The obtained residue was purified by silica gel column chromatography with the use of a mixture of n-hexane and ethyl acetate (9:1) as a developing solvent to thereby give the title compound.

Workup

  1. customThe dicyclohexyl urea thus precipitated
  2. filtrationwas filtered
  3. customThe obtained residue was purified by silica gel column chromatography with the use of a mixture of n-hexane and ethyl acetate (9:1) as a developing solvent

Sources & evidence

ORD record
ord-9090ab596a9d41038443b6518b4bfe2e
Source dataset
uspto-grants-1993_04
Patent number
US05200111

Reaction notes

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