Dicyclohexylcarbodiimide → HCID 21468106, compound

HRID 1939724Notes

Reaction equation

HRID 1939724 reaction equation
[CH3:1][C:2]([CH3:21])=[CH:3][CH2:4][C@@H:5]([OH:20])[C:6]1[C:16](=[O:17])[C:15]2[C:14]([OH:18])=[CH:13][CH:12]=[C:11]([OH:19])[C:10]=2[C:8](=[O:9])[CH:7]=1.C1(N=C=NC2CCCCC2)CCCCC1.[C:37](O)(=[O:44])[CH2:38][CH2:39][CH2:40][CH2:41][CH:42]=[CH2:43]>CN(C)C1C=CN=CC=1.ClCCl>[C:37]([O:20][CH:5]([C:6]1[C:16](=[O:17])[C:15]2[C:10]([C:8](=[O:9])[CH:7]=1)=[C:11]([OH:19])[CH:12]=[CH:13][C:14]=2[OH:18])[CH2:4][CH:3]=[C:2]([CH3:21])[CH3:1])(=[O:44])[CH2:38][CH2:39][CH2:40][CH2:41][CH:42]=[CH2:43]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 707056-Heptenoic acidHCID 479503Shikonin

Product 1

HCID 21468106HCID 21468106, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

288 mg (1 mmole) of shikonin, 226 mg (1.1 mmole) of dicyclohexylcarbodiimide and 30 mg (0.25 mmole) of 4-dimethylaminopyridine were dissolved in 3 ml of dry dichloromethane. To the resulting solution was added 128 mg (1 mmole) of 6-heptenoic acid at 0° C. under nitrogen gas, and the mixture was stirred for 30 minutes and then at room temperature for further 3 hours. The resulting product was separated and purified according to the procedures as described in Example 1 to obtain 175 mg (Yield: 44%) of the title compound having the following structure as a red precipitate.

Workup

  1. waitat room temperature for further 3 hours
  2. customThe resulting product was separated
  3. custompurified

Sources & evidence

ORD record
ord-e93307e8567b48a5884ec52d5e4b33f5
Source dataset
uspto-grants-1997_12
Patent number
US05696276

Reaction notes

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