Dichloromethane → HCID 21031078, compound

HRID 1830337Notes

Reaction equation

HRID 1830337 reaction equation
CN([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1)C.Cl.[CH2:11](N=C=NCCCN(C)C)[CH3:12].[CH3:22][O:23][C:24]1[C:25](=[O:48])[C:26]([CH3:47])=[C:27]([CH2:33][C:34]2[CH:35]=[CH:36][C:37]([O:43]C(=O)C)=[C:38]([CH:42]=2)[C:39](O)=[O:40])[C:28](=[O:32])[C:29]=1[O:30][CH3:31].[CH2:49](Cl)Cl>>[CH3:22][O:23][C:24]1[C:25](=[O:48])[C:26]([CH3:47])=[C:27]([CH2:33][C:34]2[CH:35]=[CH:36][C:37]([OH:43])=[C:38]([CH:42]=2)[C:39]([NH:5][C@@H:6]([C:7]2[CH:12]=[CH:11][CH:4]=[CH:9][CH:8]=2)[CH3:49])=[O:40])[C:28](=[O:32])[C:29]=1[O:30][CH3:31]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 218852-DimethylaminopyridineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 220542715-(5,6-Dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoic Acid

Product 1

HCID 21031078HCID 21031078, compoundYield 52%

Procedure

(R)-Phenethylamine (0.162 g, 1.337 mmol), dimethylaminopyridine (0.016 g, 0.134 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.384 g, 2.005 mmol) were added to a methylene chloride solution (30 ml) of 5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoic acid (0.250 g, 0.668 mmol) and the resulting solution was stirred at room temperature for 12 hours. The reaction solution was poured into ice water and then extracted with methylene chloride. The extract was washed with water and then dried, and the solvent was removed by distillation. The obtained residue was purified by preparative thin-layer chromatography (hexand:ethyl acetate=2:1) and then recrystallized from ether to obtain the titled compound (0.167 g, 0.350 mmol, 52%).

Workup

  1. extractionextracted with methylene chloride
  2. washThe extract was washed with water
  3. customdried
  4. customthe solvent was removed by distillation
  5. customThe obtained residue was purified by preparative thin-layer chromatography (hexand:ethyl acetate=2:1)
  6. customrecrystallized from ether

Sources & evidence

ORD record
ord-9f605a998ef74cffb77ec3c88e2256e3
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

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