Hydrochloric Acid → 1-(Allyloxycarbonyl)-7-[4-(2-butoxyethoxy)phenyl]-2,3-dihydro-1-benzazepine-4-carboxylic acid

HRID 587063Notes

Reaction equation

HRID 587063 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[C:13]2[CH:14]=[CH:15][C:16]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][O:27][CH2:28][CH2:29][CH2:30][CH3:31])=[CH:20][CH:19]=3)=[CH:17][C:12]=2[CH:11]=[C:10]([C:32]([O:34]C)=[O:33])[CH2:9][CH2:8]1)=[O:6])[CH:2]=[CH2:3].[OH-].[Na+].Cl>C1COCC1.C(O)C>[CH2:1]([O:4][C:5]([N:7]1[C:13]2[CH:14]=[CH:15][C:16]([C:18]3[CH:19]=[CH:20][C:21]([O:24][CH2:25][CH2:26][O:27][CH2:28][CH2:29][CH2:30][CH3:31])=[CH:22][CH:23]=3)=[CH:17][C:12]=2[CH:11]=[C:10]([C:32]([OH:34])=[O:33])[CH2:9][CH2:8]1)=[O:6])[CH:2]=[CH2:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22328895Methyl 1-(allyloxycarbonyl)-7-[4-(2-butoxyethoxy)phenyl]-2,3-dihydro-1-benzazepine-4-carboxylate

Product 1

HCID 223291421-(Allyloxycarbonyl)-7-[4-(2-butoxyethoxy)phenyl]-2,3-dihydro-1-benzazepine-4-carboxylic acidYield 85.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

In THF (4.5 ml)/ethanol (4.5 ml) was dissolved methyl 1-(allyloxycarbonyl)-7-[4-(2-butoxyethoxy)phenyl]-2,3-dihydro-1-benzazepine-4-carboxylate (0.30 g). To the solution was added 1N sodium hydroxide (3.0 ml), and the mixture was stirred at room temperature for 4 hours. pH was adjusted to approximate 4 with 1N hydrochloric acid, and the solvent was concentrated to half under reduced pressure. The concentrated material was extracted with ethyl acetate, the extract was washed with saturated brine and dried with magnesium sulfate. The solvent was removed under reduced pressure, and the resulting residue was washed with hexane/ethyl acetate (=8/1) to give 1-(allyloxycarbonyl)-7-[4-(2-butoxyethoxy)phenyl]-2,3-dihydro-1-benzazepine-4-carboxylic acid (0.25 g).

Workup

  1. concentrationthe solvent was concentrated to half under reduced pressure
  2. extractionThe concentrated material was extracted with ethyl acetate
  3. washthe extract was washed with saturated brine
  4. dry with materialdried with magnesium sulfate
  5. customThe solvent was removed under reduced pressure
  6. washthe resulting residue was washed with hexane/ethyl acetate (=8/1)

Sources & evidence

ORD record
ord-0cba0a0905f940c385014cbe75d076a0
Source dataset
uspto-grants-2005_08
Patent number
US06936602B1

Reaction notes

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