Chloroacetic Acid → HCID 86751715, compound

HRID 1939718

Reaction equation

HRID 1939718 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.[Cl:37][CH2:38][C:39](O)=[O:40]>CN(C)C1C=CN=CC=1.ClCCl>[Cl:37][CH2:38][C:39]([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:40]

Participants

6

Reactant 3

HCID 300Chloroacetic AcidHCID 10868DicyclohexylcarbodiimideHCID 479503Shikonin

Product 1

HCID 86751715HCID 86751715, compoundYield 60%

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 3ml of dry dichloromethane. To the resulting solution was added 94.5 mg (1 mmole) of monochloroacetic 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 procedure as described in Example 1 to obtain 218 mg (Yield: 60%) of the title compound having the following structure as a red oil.

Workup

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

Sources & evidence

ORD record
ord-be26e789d0aa495bad6e76b990fcdcf9
Source dataset
uspto-grants-1997_12
Patent number
US05696276

Linked notes

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