Dicyclohexylcarbodiimide → HCID 178443711, compound

HRID 1780566Notes

Reaction equation

HRID 1780566 reaction equation
[F:1][C:2]1[C:7]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[CH:6][CH:5]=[C:4]([C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=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.ClCCl>[CH2:39]([C@H:44]1[CH2:45][CH2:46][C@H:47]([C:50]([O:23][C:20]2[CH:19]=[CH:18][C:17]([C:4]3[N:3]=[C:2]([F:1])[C:7]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[CH:6][CH:5]=3)=[CH:22][CH:21]=2)=[O:51])[CH2:48][CH2:49]1)[CH2:40][CH2:41][CH2:42][CH3:43]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 1357947772-Fluoro-6-(4-hydroxyphenyl)-3-octyloxypyridineHCID 178444557HCID 178444557, compound

Product 1

HCID 178443711HCID 178443711, compoundYield 57.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

1.11 g (3.50 mmol) of 2-fluoro-6-(4-hydroxyphenyl)-3-octyloxypyridine, 0.72 g (3.50 mmol) of dicyclohexylcarbodiimide, 0.69 g (3.50 mmol) of trans-4-pentylcyclohexanecarboxylic acid and 0.02 g of 4-(N,N-dimethylamino)pyridine are stirred in 20 ml of dichloromethane at room temperature for 3 hours. After filtration of the mixture, evaporation of the filtrate to dryness, purification of the residue by chromatography (silica gel, 8:2 hexane/ethyl acetate) and recrystallization from n-hexane, 1.00 g of 4-(2-fluoro-3-octyloxypyridine-6-yl)phenyl trans-4-pentylcyclohexanecarboxylate is obtained. ##STR48##

Workup

  1. filtrationAfter filtration of the mixture, evaporation of the filtrate
  2. customto dryness, purification of the residue
  3. customby chromatography (silica gel, 8:2 hexane/ethyl acetate) and recrystallization from n-hexane

Sources & evidence

ORD record
ord-d9913c0bafdf4bab90098e0bf63a2397
Source dataset
uspto-grants-1997_05
Patent number
US05630962

Reaction notes

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