Dicyclohexylcarbodiimide → HCID 18650840, compound

HRID 1609421Notes

Reaction equation

HRID 1609421 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-pyrrolidinopyridine 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-4e03ef278961462db8cd98cb2ecbfc1a
Source dataset
uspto-grants-1995_03
Patent number
US05401436

Reaction notes

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