(2-Methoxyethyl)(methyl)amine → HCID 11995810, compound

HRID 499875Notes

Reaction equation

HRID 499875 reaction equation
[CH2:1]([C:3]1[C:8]([OH:9])=[CH:7][C:6]([OH:10])=[C:5]([C:11](=[O:20])[C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[C:4]=1[CH2:21][C:22]([OH:24])=O)[CH3:2].O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[CH3:48][O:49][CH2:50][CH2:51][NH:52][CH3:53]>ClCCl.O>[CH2:1]([C:3]1[C:8]([OH:9])=[CH:7][C:6]([OH:10])=[C:5]([C:11](=[O:20])[C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[C:4]=1[CH2:21][C:22]([N:52]([CH2:51][CH2:50][O:49][CH3:48])[CH3:53])=[O:24])[CH3:2]

Participants

7

Reactant 4

HCID 300977(2-Methoxyethyl)(methyl)amineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 23116272HCID 23116272, compound

Product 1

HCID 11995810HCID 11995810, compoundYield 13.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

2-Ethyl-3,5-dihydroxy-6-(4-methoxybenzoyl)phenyl-acetic acid (0.18 g, 0.53 mmol) obtained in Example 10, Step 1 was dissolved in dichloromethane (2.0 mL). To the solution were added 1-hydroxybenzotriazole hydrate (0.11 g, 0.72 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.14 g, 0.72 mmol) and 2-methoxy-N-methylethylamine (0.12 mL, 1.1 mmol), followed by stirring at room temperature for 14 hours. To the reaction mixture was added water (10 mL), and the mixture was extracted with chloroform (50 mL×2). The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resulting residue was purified by preparative thin layer chromatography (methanol/chloroform=1/9) to obtain Compound 10 (28 mg, 13%).

Workup

  1. extractionthe mixture was extracted with chloroform (50 mL×2)
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by preparative thin layer chromatography (methanol/chloroform=1/9)

Sources & evidence

ORD record
ord-849fbd712d44449fa91c556989bd9309
Source dataset
uspto-grants-2010_08
Patent number
US07767693B2

Reaction notes

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