Hydrochloric Acid → HCID 59304065, compound

HRID 544805Notes

Reaction equation

HRID 544805 reaction equation
[OH:1][CH:2]([CH3:15])[CH2:3][C:4]([CH:6]1[C:11]([CH3:13])([CH3:12])[CH2:10][CH2:9][CH:8]=[C:7]1[CH3:14])=[O:5].[CH3:16][N:17]([C:19]1[CH:24]=[C:23]([C:25](O)=[O:26])[CH:22]=[CH:21][CH:20]=1)[CH3:18].C1CCC(N=C=NC2CCCCC2)CC1.Cl>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:16][N:17]([CH3:18])[C:19]1[CH:24]=[C:23]([CH:22]=[CH:21][CH:20]=1)[C:25]([O:1][CH:2]([CH3:15])[CH2:3][C:4](=[O:5])[CH:6]1[C:11]([CH3:13])([CH3:12])[CH2:10][CH2:9][CH:8]=[C:7]1[CH3:14])=[O:26]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10868DicyclohexylcarbodiimideHCID 668373-(Dimethylamino)benzoic acidHCID 23456997HCID 23456997, compound

Product 1

HCID 59304065HCID 59304065, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-hydroxy-1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-1-butanone (4.00 g, 92% pure, 17.5 mmol), 3-N,N-dimethylaminobenzoic acid (3.13 g, 19.0 mmol), and DMAP (1.85 g, 15.2 mmol) in CH2Cl2 (50 ml) was added N,N′-dicyclohexylcarbodiimine (DCC) (4.31 g, 20.9 mmol) in CH2Cl2 (15 ml). The reaction medium was stirred at room temperature for 70 h. Then, the mixture was acidified with concentrated HCl and extracted twice with ether and washed with water, saturated aqueous NaHCO3 and then with saturated aqueous NaCl. Finally, the organic phases were dried over Na2SO4, concentrated at 50-60°/0.03 mbar) and purified by flash-chromatography over SiO2 (cyclohexane/AcOEt=97:3). 4.20 g of product were thus obtained (yield: 68%).

Workup

  1. extractionextracted twice with ether
  2. washwashed with water, saturated aqueous NaHCO3
  3. dry with materialFinally, the organic phases were dried over Na2SO4
  4. concentrationconcentrated at 50-60°/0.03 mbar) and
  5. custompurified by flash-chromatography over SiO2 (cyclohexane/AcOEt=97:3)

Sources & evidence

ORD record
ord-2a6c89033b834bac9051c820d11061de
Source dataset
uspto-grants-2011_05
Patent number
US07935669B2

Reaction notes

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