Dicyclohexylcarbodiimide → HCID 178443712, compound

HRID 1780561Notes

Reaction equation

HRID 1780561 reaction equation
[F:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([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:3]=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.C(Cl)Cl>[CH2:39]([C@H:44]1[CH2:45][CH2:46][C@H:47]([C:50]([O:8][C:7]2[C:2]([F:1])=[N:3][C:4]([C:9]3[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]=3)=[CH:5][CH:6]=2)=[O:51])[CH2:48][CH2:49]1)[CH2:40][CH2:41][CH2:42][CH3:43]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 190469612-(4-Octyloxyphenyl)-5-hydroxy-6-fluoropyridineHCID 178444557HCID 178444557, compound

Product 1

HCID 178443712HCID 178443712, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

0.29 g (0.91 mmol) of 2-fluoro-3-hydroxy-6-(4-octyloxyphenyl)pyridine (prepared as described in Example 3), 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 in 10 ml of methylene chloride at room temperature for 18 hours. Filtration, evaporation to dryness, purification by chromatography (silica gel, 8:2 hexane/ethyl acetate) and recrystallization from acetonitrile give 0.19 g of 2-fluoro-6-(4-octyloxyphenyl)pyridin-3-yl trans-4-pentylcyclohexanecarboxylate. ##STR40##

Workup

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

Sources & evidence

ORD record
ord-45f858c4754e475fbef9c5d31554409c
Source dataset
uspto-grants-1997_05
Patent number
US05630962

Reaction notes

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