Dicyclohexylcarbodiimide → HCID 14692538, compound

HRID 1089087Notes

Reaction equation

HRID 1089087 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C@@H:7]([OH:9])[CH3:8])[CH:2]=1.[CH2:10]([O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][C:28]([C:31](O)=[O:32])=[CH:27][CH:26]=2)=[CH:21][CH:20]=1)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].C1(N=C=NC2CCCCC2)CCCCC1.CN(C1C=CC=CN=1)C>C(Cl)Cl>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C@@H:7]([O:9][C:31]([C:28]2[CH:27]=[CH:26][C:25]([C:22]3[CH:23]=[CH:24][C:19]([O:18][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:20][CH:21]=3)=[CH:30][CH:29]=2)=[O:32])[CH3:8])[CH:2]=1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 218852-DimethylaminopyridineHCID 28025564'-(Octyloxy)-[1,1'-biphenyl]-4-carboxylic acidHCID 10725338(S)-1-(3-Pyridyl)ethanol2×

Product 1

HCID 14692538HCID 14692538, compoundYield 7.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-1-(3-pyridyl)ethanol (2.0 g) prepared in the above item (ii), 4-octyloxybiphenyl-4'-carboxylic acid (5.3 g), dicyclohexylcarbodiimide (5.7 g) and dimethylaminopyridine (0.2 g) were dissolved in methylene chloride (100 ml), followed by agitating the solution for 15 hours, thereafter filtering off insolubles, washing the filtrate with water, concentrating it and recrystallizing from a mixed solvent of heptane-toluene to obtain (S)-4-octyloxybiphenyl-4'-carboxylic acid-1-(3-pyridyl)ethyl ester (0.5 g). M.P.: 77.5-78.5° C. Specific angle of rotation [a]D25 =+95° (c=1.0, CHCl3). Further, the structure of this product was confirmed according to NMR spectra and the product accorded with the captioned compound.

Workup

  1. filtrationfiltering off insolubles
  2. washwashing the filtrate with water
  3. concentrationconcentrating it
  4. customrecrystallizing from a mixed solvent of heptane-toluene

Sources & evidence

ORD record
ord-1404b9a84baa494c8d85e9e7b695d557
Source dataset
uspto-grants-1990_10
Patent number
US04965018

Reaction notes

Loading…