Dichloromethane → HCID 21031079, compound

HRID 1830336Notes

Reaction equation

HRID 1830336 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 21031079HCID 21031079, compoundYield 53%

Procedure

(S)-Phenethylamine (0.130 g, 1.07 mmol), dimethylaminopyridine (0.013 g, 0.107 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.308 g, 1.60 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 (0.200 g, 0.535 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 (0.135 g, 0.283 mmol, 53%).

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-80a84b1cba7a45b5aa8bdc7a99d2262f
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

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