Dicyclohexylcarbodiimide → HCID 68127367, compound

HRID 2398894Notes

Reaction equation

HRID 2398894 reaction equation
[CH3:1][C:2]1([CH3:32])[C:7]2[CH2:8][CH2:9][CH2:10][C:6]=2[C:5]2[C:11]([OH:31])=[CH:12][C:13]([C:15]([C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)([CH3:23])[CH2:16][CH2:17][CH2:18]CCCC)=[CH:14][C:4]=2[O:3]1.[ClH:33].[N:34]1([CH2:39][CH2:40][CH2:41][C:42](O)=[O:43])[CH2:38][CH2:37][CH2:36][CH2:35]1.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[ClH:33].[CH3:32][C:2]1([CH3:1])[C:7]2[CH2:8][CH2:9][CH2:10][C:6]=2[C:5]2[C:11]([O:31][C:42](=[O:43])[CH2:41][CH2:40][CH2:39][N:34]3[CH2:38][CH2:37][CH2:36][CH2:35]3)=[CH:12][C:13]([C:15]([C:24]3[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=3)([CH3:23])[CH2:16][CH2:17][CH3:18])=[CH:14][C:4]=2[O:3]1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 148556824-(Pyrrolidin-1-yl)butanoic acid hydrochlorideHCID 54139897HCID 54139897, compound

Product 1

HCID 68127367HCID 68127367, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3.21 g. (9.37 mmole) of 4,4-Dimethyl-9-hydroxy-7-(4-fluorophenyl-1-methyloctyl)-1,2,3,4-tetrahydrocyclopenta [c][1]benzopyran are combined with 1.82 g. (9.37 mmole) of γ-pyrrolidinobutyric acid hydrochloride and 2.06 g. (10.0 mmole) of dicyclohexylcarbodiimide in 150 ml. of methylene chloride and stirred at room temperature for 21/2 hours. The insoluble by-product of dicyclohexylurea is removed by filtration and the filtrate is evaporated to give a residue which crystallized upon standing. The material is triturated with ether and filtered. Recrystallization from benzene/ether gives the product as colorless crystals.

Workup

  1. customThe insoluble by-product of dicyclohexylurea is removed by filtration
  2. customthe filtrate is evaporated
  3. customto give a residue which
  4. customcrystallized
  5. customThe material is triturated with ether
  6. filtrationfiltered
  7. customRecrystallization from benzene/ether

Sources & evidence

ORD record
ord-8a9d58dae467402284363a62f9885228
Source dataset
uspto-grants-1977_05
Patent number
US04025630

Reaction notes

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