Dicyclohexylcarbodiimide → HCID 54346421, compound

HRID 1650650Notes

Reaction equation

HRID 1650650 reaction equation
[CH2:1]([O:13][C:14]1[CH:29]=[CH:28][C:17]([C:18]([O:20][C:21]2[CH:26]=[CH:25][C:24](O)=[CH:23][CH:22]=2)=[O:19])=[CH:16][C:15]=1[Cl:30])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[O:31]1CCCC[CH:32]1[O:37][CH:38]([CH2:43][CH2:44]CCCC)CC(O)=O.C1(N=C=N[CH:58]2[CH2:63][CH2:62][CH2:61][CH2:60][CH2:59]2)CCCCC1.N1(C2C=CN=CC=2)CCCC1.C1(C)C=CC(S([O-])(=O)=[O:82])=CC=1.[NH+]1C=CC=CC=1>C(Cl)Cl.C(OCC)(=O)C.C(O)C.C(Cl)(Cl)Cl.CCCCCC>[CH2:1]([O:13][C:14]1[CH:29]=[CH:28][C:17]([C:18]([O:20][C:21]2[CH:26]=[CH:25][C:24]([C:32]([O:37][CH2:38][CH:43]([OH:82])[CH2:44][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH3:58])=[O:31])=[CH:23][CH:22]=2)=[O:19])=[CH:16][C:15]=1[Cl:30])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

11

Reactant 5

HCID 10868DicyclohexylcarbodiimideHCID 755674-PyrrolidinopyridineHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 14692539HCID 14692539, compoundHCID 23052148HCID 23052148, compound

Product 1

HCID 54346421HCID 54346421, compoundYield 312.4%

Reagents, catalysts & solvents 5

HCID 702EthanolSolventHCID 6212ChloroformSolvent2×HCID 6344DichloromethaneSolventHCID 8058HexaneSolvent2×HCID 8857Ethyl AcetateSolvent2×

Procedure

Then, 300 mg of 4-hydroxyphenyl 4-dodecyloxy-3-chlorobenzoate, 300 mg of β-tetrahydropyranyloxynonanoic acid, 250 mg of dicyclohexylcarbodi-imide and 25 mg of 4-pyrrolidinopyridine were dissolved in methylene chloride, and reaction was carried out at room temperature with stirring overnight. The thus-obtained solution was diluted with ethyl acetate, and the dilution was washed with a 0.5N aqueous solution of hydrochloric acid, a saturated aqueous solution of sodium chloride, a saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride in succession, dehydrated on anhydrous magnesium sulfate and concentrated. The intended product was isolated by the silica gel column chromatography using a mixed solvent of n-hexane and chloroform. The isolated product was dissolved in ethanol, 20 mg of pyridinium p-toluenesulfonate was added to the solution, and the mixture was stirred at 50° C. for 1 hour. The thus-obtained solution was diluted with ethyl acetate again, and the dilution was washed with a saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride in succession, dehydrated on anhydrous magnesium sulfate and concentrated. The intended product was isolated by the silica gel column chromatography using a mixed solvent of n-hexane and chloroform and recrystallized from ethyl acetate to obtain 150 mg of 4-(β-hydroxynonylcarboxy)phenyl 4-dodecyloxy-3-chlorobenzoate. By the NMR spectrum analysis and elementary analysis, it was confirmed that the obtained product was the intended compound. The NMR spectrum of the obtained compound is shown in FIG. 2, and the elementary analysis values are shown below.

Workup

  1. customreaction
  2. customwas carried out at room temperature
  3. washthe dilution was washed with a 0.5N aqueous solution of hydrochloric acid
  4. concentrationconcentrated
  5. customThe intended product was isolated by the silica gel column chromatography
  6. stirringthe mixture was stirred at 50° C. for 1 hour
  7. washthe dilution was washed with a saturated aqueous solution of sodium bicarbonate
  8. concentrationconcentrated
  9. customThe intended product was isolated by the silica gel column chromatography
  10. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-302b021c2bb3430cb0052d2aea6646d7
Source dataset
uspto-grants-1990_05
Patent number
US04925591

Reaction notes

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