Dicyclohexylcarbodiimide → HCID 178455753, compound

HRID 1004538Notes

Reaction equation

HRID 1004538 reaction equation
[CH2:1]([C@H:3]1[CH2:8][CH2:7][C@H:6]([C@H:9]2[CH2:14][CH2:13][C@H:12]([C:15]3[CH:23]=[CH:22][C:18]([C:19]([OH:21])=[O:20])=[CH:17][CH:16]=3)[CH2:11][CH2:10]2)[CH2:5][CH2:4]1)[CH3:2].[F:24][C:25]1[CH:26]=[C:27](O)[CH:28]=[C:29]([F:33])[C:30]=1[CH2:31][F:32].C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.ClCCl>[CH2:1]([C@H:3]1[CH2:8][CH2:7][C@H:6]([C@H:9]2[CH2:10][CH2:11][C@H:12]([C:15]3[CH:23]=[CH:22][C:18]([C:19]([O:21][C:27]4[CH:26]=[C:25]([F:24])[C:30]([CH2:31][F:32])=[C:29]([F:33])[CH:28]=4)=[O:20])=[CH:17][CH:16]=3)[CH2:13][CH2:14]2)[CH2:5][CH2:4]1)[CH3:2]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 18792308HCID 18792308, compoundHCID 178455754HCID 178455754, compound

Product 1

HCID 178455753HCID 178455753, compoundYield 95.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

First, 1.5 g (4.8 mmol) of 4-(trans-4-(trans-4-ethylcyclohexyl)cyclohexyl)benzoic acid, 0.8 g (4.8 mmol) of 3,5-difluoro-4-fluoromethylphenol, 0.2 g (1.4 mmol) of DMAP, and 25 ml of dichloromethane were mixed. To this mixture was added dropwise 5 ml of dichoromethane solution containing 1.2 g (5.7 mmol) of DCC at room temperature in 5 minutes, and reacted as they were while stirring for 12 hours. The crystal thus precipitated were filtered off. Toluene in an amount of 30 ml was added to the filtrate, and washed with 2N-sodium hydroxide 5 times and water thrice, and then dried over anhydrous magnesium sulfate. Solvent was distilled off at a reduced pressure and the residue was subjected to a silica gel column chromatography (eluent: toluene) to obtain 2.1 g of a crude 3,5-difluoro-4-fluoromethylphenyl 4-(trans-4-(trans-4-ethylcyclohexyl) cyclohexyl)benzoate. This product was recrystallized from a mixed solvent of heptane/ethyl (1/1) acetate to obtain 1.9 g (yield: 86.3%) of the subject compound.

Workup

  1. customreacted as they
  2. customThe crystal thus precipitated
  3. filtrationwere filtered off
  4. additionToluene in an amount of 30 ml was added to the filtrate
  5. washwashed with 2N-sodium hydroxide 5 times and water thrice
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationSolvent was distilled off at a reduced pressure

Sources & evidence

ORD record
ord-ca214fe570b143a19f86b344dc38c42c
Source dataset
uspto-grants-2000_04
Patent number
US06051288

Reaction notes

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