Hydrochloric Acid → HCID 69558143, compound

HRID 1833166Notes

Reaction equation

HRID 1833166 reaction equation
C(OC(=O)[N:5]([CH2:29][CH:30](OC)OC)[CH:6]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][CH2:25][OH:26])=[C:18]([O:27][CH3:28])[CH:17]=1)[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[CH:9]=1)C.Cl.[C:37]([O:40][CH2:41][CH3:42])(=[O:39])C.CCCCCC>CC(C)=O.O>[CH2:41]([O:40][C:37]([N:5]1[CH:29]=[CH:30][C:21]2[C:16](=[CH:17][C:18]([O:27][CH3:28])=[C:19]([O:22][CH2:23][CH2:24][CH2:25][OH:26])[CH:20]=2)[CH:6]1[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[CH:9]=1)=[O:39])[CH3:42]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 21226206Ethyl acetate hexaneHCID 69552487(2,2-Dimethoxy-ethyl)-[1-[4-(3-hydroxy-propoxy)-3-methoxy-phenyl]-2-(3-methoxy-phenyl)-ethyl]-carbamic acid ethyl ester

Product 1

HCID 69558143HCID 69558143, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a stirred solution of crude (2,2-dimethoxy-ethyl)-[1-[4-(3-hydroxy-propoxy)-3-methoxy-phenyl]-2-(3-methoxy-phenyl)-ethyl]-carbamic acid ethyl ester in acetone (30 mL) was added 6N hydrochloric acid (10 mL) at 0° C. The reaction mixture was stirred at room temperature for 15 hrs. The mixture was diluted with water. The solvent was evaporated and the aqueous layer was extracted with ethyl acetate (3×30 mL). The combined extracts were washed with saturated aqueous sodium chloride solution (20 mL), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 70–230 mesh, 50% ethyl acetate/hexane) afforded 6-(3-hydroxy-propoxy)-7-methoxy-1-(3-methoxy-benzyl)-1H-isoquinoline-2-carboxylic acid ethyl ester (130, 32% yield in two steps) as a colorless oil.

Workup

  1. customThe solvent was evaporated
  2. extractionthe aqueous layer was extracted with ethyl acetate (3×30 mL)
  3. washThe combined extracts were washed with saturated aqueous sodium chloride solution (20 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ad5b78ea5ea24115b18997e44db8506f
Source dataset
uspto-grants-2006_06
Patent number
US07067529B2

Reaction notes

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