Dicyclohexylcarbodiimide → HCID 178443715, compound

HRID 1780068Notes

Reaction equation

HRID 1780068 reaction equation
[Cl:1][C:2]1[C:3]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:11][CH:10]=2)=[N:4][CH:5]=[C:6]([OH:8])[CH:7]=1.C1(N=C=NC2CCCCC2)CCCCC1.[CH2:39]([C@H:44]1[CH2:49][CH2:48][C@H:47]([C:50](O)=[O:51])[CH2:46][CH2:45]1)[CH2:40][CH2:41][CH2:42][CH3:43]>CN(C1C=CN=CC=1)C.ClCCl>[CH2:39]([C@H:44]1[CH2:45][CH2:46][C@H:47]([C:50]([O:8][C:6]2[CH:7]=[C:2]([Cl:1])[C:3]([C:9]3[CH:10]=[CH:11][C:12]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:13][CH:14]=3)=[N:4][CH:5]=2)=[O:51])[CH2:48][CH2:49]1)[CH2:40][CH2:41][CH2:42][CH3:43]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 190499953-Chloro-5-hydroxy-2-(4-octyloxyphenyl)pyridineHCID 178444557HCID 178444557, compound

Product 1

HCID 178443715HCID 178443715, compoundYield 21.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

0.78 g (2.50 mmol) of 3-chloro-5-hydroxy-2-(4-octyloxyphenyl)pyridine, 0.52 g (2.50 mmol) of dicyclohexylcarbodiimide, 0.50 g (2.50 mmol) of trans-4-pentylcyclohexanecarboxylic acid and 0.01 g of 4-(N,N-dimethylamino)-pyridine are stirred at room temperature for 18 hours in 20 ml of dichloromethane. Filtration, evaporation to dryness and chromatographic purification (silica gel/ hexane:ethyl acetate 8:2) and recrystallization from acetonitrile give 0.28 g of 3-chloro-2-(4-octyloxyphenyl)pyridin-5-yl trans-4-pentylcyclohexanecarboxylate. ##STR26##

Workup

  1. filtrationFiltration, evaporation
  2. customto dryness and chromatographic purification (silica gel/ hexane:ethyl acetate 8:2) and recrystallization from acetonitrile

Sources & evidence

ORD record
ord-3c072e67a96c41aca6cc154b14397a8d
Source dataset
uspto-grants-1997_05
Patent number
US05629428

Reaction notes

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