Hydrogen chloride-ethyl acetate → HCID 67537382, compound

HRID 2383073Notes

Reaction equation

HRID 2383073 reaction equation
[CH:1]1([CH:7]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH3:18])[CH:15]=3)[CH2:10][CH2:9][N:8]2[C:19](=[O:34])[CH2:20][NH:21][CH2:22][CH2:23][O:24][C@@H:25]2[CH2:29][CH2:28][CH2:27][C@@H:26]2[O:30]COC)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.CCOC(C)=O>CO>[CH:1]1([CH:7]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH3:18])[CH:15]=3)[CH2:10][CH2:9][N:8]2[C:19](=[O:34])[CH2:20][NH:21][CH2:22][CH2:23][O:24][C@H:25]2[CH2:29][CH2:28][CH2:27][C@H:26]2[OH:30])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 67537790HCID 67537790, compound

Product 1

HCID 67537382HCID 67537382, compoundYield 83.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

2-(1-cyclohexyl-7-methoxy-3,4-dihydroisoquinolin-2(1H)-yl)-N-(2-{[cis-2-(methoxymethoxy)cyclopentyl]oxy}ethyl)-2-oxoethanamine (500 mg) was dissolved in MeOH (8 mL). To the reaction liquid was added 4 M HCl/EtOAc (0.8 mL) under ice-cooling, followed by stirring at 60° C. for 5 hours. The solvent was evaporated and saturated aqueous sodium bicarbonate was added to the resulting residue, followed by extraction with chloroform. The extract was washed with saturated brine, and then dried over magnesium sulfate. The solvent was evaporated and the resulting residue was purified by silica gel column chromatography (chloroform-MeOH) to obtain cis-2-(2-{[2-(1-cyclohexyl-7-methoxy-3,4-dihydroisoquinolin-2(1H)-yl)-2-oxoethyl]amino}ethoxy)cyclopentanol (380 mg).

Workup

  1. customTo the reaction liquid
  2. temperaturecooling
  3. customThe solvent was evaporated
  4. additionsaturated aqueous sodium bicarbonate was added to the resulting residue
  5. extractionfollowed by extraction with chloroform
  6. washThe extract was washed with saturated brine
  7. dry with materialdried over magnesium sulfate
  8. customThe solvent was evaporated
  9. customthe resulting residue was purified by silica gel column chromatography (chloroform-MeOH)

Sources & evidence

ORD record
ord-949efe20915e485b9a0d05d9a9dfe2fb
Source dataset
uspto-grants-2012_09
Patent number
US08263607B2

Reaction notes

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