Dicyclohexylcarbodiimide → HCID 178443716, compound

HRID 1757363Notes

Reaction equation

HRID 1757363 reaction equation
[F: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]([F: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 19387549HCID 19387549, compoundHCID 178444557HCID 178444557, compound

Product 1

HCID 178443716HCID 178443716, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

0.29 g (0.91 mmol) of 3-fluoro-5-hydroxy-2-(4-octyloxyphenyl)pyridine, 0.19 g (0.91 mmol) of dicyclohexylcarbodiimide, 0.16 g (0.91 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 10 ml of dichloromethane. Filtration, evaporation to dryness, chromatographic purification (silica gel/hexane: ethyl acetate 8:2) and recrystallization from acetonitrile give 0.19 g of 3-fluoro-2-(4-octyloxyphenyl)pyridin-5-yl trans-4-pentylcyclohexanecarboxylate. ##STR28## The compound has the phase sequence: X 65.2 (40.2) Sc 63 SA 129 N 173 I.

Workup

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

Sources & evidence

ORD record
ord-71066c13a63240f9901ba2736a1158ed
Source dataset
uspto-grants-1995_08
Patent number
US05445763

Reaction notes

Loading…