Dicyclohexylcarbodiimide → HCID 18650840, compound

HRID 1589765Notes

Reaction equation

HRID 1589765 reaction equation
[Cl:1][C@@H:2]([CH3:22])[CH2:3][C@H:4]([CH3:21])[O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:20]=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=2)=[CH:8][CH:7]=1.[CH2:23]([C:26]1[CH:31]=[CH:30][C:29](O)=[CH:28][CH:27]=1)[CH2:24][CH3:25].C1(N=C=NC2CCCCC2)CCCCC1.N1(C2C=CN=CC=2)CCCC1>C(Cl)Cl>[CH2:23]([C:26]1[CH:31]=[CH:30][C:29]([O:17][C:16](=[O:18])[C:15]2[CH:19]=[CH:20][C:12]([C:9]3[CH:8]=[CH:7][C:6]([O:5][C@@H:4]([CH3:21])[CH2:3][C@@H:2]([Cl:1])[CH3:22])=[CH:11][CH:10]=3)=[CH:13][CH:14]=2)=[CH:28][CH:27]=1)[CH2:24][CH3:25]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 125804-PropylphenolHCID 755674-PyrrolidinopyridineHCID 18650841HCID 18650841, compound

Product 1

HCID 18650840HCID 18650840, compoundYield 62.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.47 g of (S,S)-4-[4'-(3"-chloro-1"-methylbutoxy)-phenyl]benzoic acid, 0.20 g of 4-n-propylphenol, 0.32 g of dicyclohexylcarbodiimide, 0.04 g of 4-pyrrolidino-pyridine and 6 ml of methylene chloride were stirred together at room temperature for five hours. The dicyclohexyl urea thus precipitated was filtered and the filtrate was desolvated. The crude product thus obtained was purified by silica gel column chromatography with the use of a mixture of n-hexane and ethyl acetate (17:3) as a developing solvent. Thus 0.4 g of the title compound was obtained.

Workup

  1. customThe dicyclohexyl urea thus precipitated
  2. filtrationwas filtered
  3. customThe crude product thus obtained
  4. customwas purified by silica gel column chromatography with the use of a mixture of n-hexane and ethyl acetate (17:3) as a developing solvent

Sources & evidence

ORD record
ord-169a7246fe894863b25f476fabab859e
Source dataset
uspto-grants-1993_04
Patent number
US05200111

Reaction notes

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