Dicyclohexylcarbodiimide → HCID 22852310, compound

HRID 1609422Notes

Reaction equation

HRID 1609422 reaction equation
[Cl:1][C@@H:2]([CH3:16])[CH2:3][C@H:4]([CH3:15])[O:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[CH:8][CH:7]=1.[CH2:17]([O:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2O)=[CH:24][CH:23]=1)[CH2:18][CH2:19][CH3:20].C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[CH2:17]([O:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2[CH:33]=[CH:32][C:31]([O:11][C:10](=[O:12])[C:9]3[CH:13]=[CH:14][C:6]([O:5][C@@H:4]([CH3:15])[CH2:3][C@@H:2]([Cl:1])[CH3:16])=[CH:7][CH:8]=3)=[CH:30][CH:29]=2)=[CH:24][CH:23]=1)[CH2:18][CH2:19][CH3:20]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 18650833HCID 18650833, compoundHCID 20081236HCID 20081236, compound

Product 1

HCID 22852310HCID 22852310, compoundYield 49.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.21 g of (S, S)-4-(3'-chloro-1'-methylbutoxy)benzoic acid, 0.21 g of 4-n-butoxyphenyl phenol, 0.19 g of dicyclohexylcarbodiimide, 0.03 g of 4-pyrrolidinopyridene 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 (9:1) as a developing solvent to thereby give 0.2 g of the title compound.

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 (9:1) as a developing solvent

Sources & evidence

ORD record
ord-f1aa36fe876c4d2a87635baaa585cfaf
Source dataset
uspto-grants-1995_03
Patent number
US05401436

Reaction notes

Loading…