Hydrochloric Acid → HCID 86600514, compound

HRID 1766396Notes

Reaction equation

HRID 1766396 reaction equation
[CH2:1]1[CH:10]2[CH:5]([CH2:6][CH2:7][CH2:8][CH:9]2[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:4][CH2:3][NH:2]1.CN(C)CCCN=C=NCC.[F:27][C:28]1[CH:33]=[CH:32][C:31]([CH2:34][CH2:35][C:36](O)=[O:37])=[CH:30][CH:29]=1.Cl>ClCCl>[F:27][C:28]1[CH:29]=[CH:30][C:31]([CH2:34][CH2:35][C:36]([N:2]2[CH2:3][CH2:4][CH:5]3[CH:10]([CH:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:8][CH2:7][CH2:6]3)[CH2:1]2)=[O:37])=[CH:32][CH:33]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 1363023-(4-Fluorophenyl)propionic acidHCID 86600513HCID 86600513, compound

Product 1

HCID 86600514HCID 86600514, compoundYield 82.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of ethyl (4aSR,8SR,8aSR)-decahydroisoquinoline-8-carboxylate (273 mg, 1.29 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide (309 mg, 1.61 mmol) in dichloromethane (10 mL) was treated with 3-(4-fluorophenyl)propanoic acid (271 m, 1.61 mmol). The mixture was stirred at room temperature for 4 hours, and then treated with 1.0 N aqueous hydrochloric acid. The mixture was extracted with dichloromethane (3×5 mL), and the combined organic phases were washed with 1.0 N aqueous sodium hydroxide, dried over magnesium sulfate and concentrated to provide a residue. The residue was purified by radial thin layer chromatography, eluting with 33% ethyl acetate/hexane, to provide a colorless oil (385 mg, 82%).

Workup

  1. extractionThe mixture was extracted with dichloromethane (3×5 mL)
  2. washthe combined organic phases were washed with 1.0 N aqueous sodium hydroxide
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customto provide a residue
  6. customThe residue was purified by radial thin layer chromatography
  7. washeluting with 33% ethyl acetate/hexane

Sources & evidence

ORD record
ord-ec1522780db440c68637a11e9e2d054d
Source dataset
uspto-grants-2007_06
Patent number
US07230022B2

Reaction notes

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