Phosphorus pentachloride → HCID 69551824, compound

HRID 1833269Notes

Reaction equation

HRID 1833269 reaction equation
[CH2:1]([O:3][C:4](=[O:30])[CH:5]([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH3:29])[CH:21]=1)[CH2:6][NH:7][C:8](=O)[CH2:9][C:10]1[CH:15]=[C:14]([CH3:16])[CH:13]=[C:12]([O:17][CH3:18])[CH:11]=1)[CH3:2].P(Cl)(Cl)(Cl)(Cl)Cl.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH2:1]([O:3][C:4]([CH:5]1[C:20]2[C:25](=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH3:29])[CH:21]=2)[C:8]([CH2:9][C:10]2[CH:15]=[C:14]([CH3:16])[CH:13]=[C:12]([O:17][CH3:18])[CH:11]=2)=[N:7][CH2:6]1)=[O:30])[CH3:2]

Participants

5

Reactant 3

HCID 24819Phosphorus pentachlorideHCID 516892Sodium BicarbonateHCID 69551777HCID 69551777, compound

Product 1

HCID 69551824HCID 69551824, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-(3,4-dimethoxy-phenyl)-3-[2-(3-methoxy-5-methyl-phenyl)-acetylamino]-propionic acid ethyl ester (0.79 g, 1.9 mmol) and phosphorus pentachloride (0.59 g, 2.85 mmol) in dry methylene chloride (25 mL) was stirred at room temperature overnight. A cold, saturated aqueous sodium bicarbonate solution (75 mL) was added to the reaction mixture and stirred for 1 hr. The layers were separated and the aqueous layer extracted with methylene chloride (2×25 mL). The combined organic layers were dried over magnesium sulfate, filtered and concentrated in vacuo to afford 6,7-dimethoxy-1-(3-methoxy-5-methyl-benzyl)-3,4-dihydro-isoquinoline-4-carboxylic acid ethyl ester as a light green oil (0.73 g, 97%). This material was used without further purification: 1H NMR (300 MHz) compatible.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer extracted with methylene chloride (2×25 mL)
  3. dry with materialThe combined organic layers were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a51f82b7467947aa934ed3e4911ef0ba
Source dataset
uspto-grants-2006_06
Patent number
US07067529B2

Reaction notes

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