Sodium Hydroxide → HCID 67490897, compound

HRID 1917370Notes

Reaction equation

HRID 1917370 reaction equation
[OH-].[Na+].C[O:4][C:5]([C:7]12[CH2:14][CH2:13][CH:12]=[C:11]1[CH2:10][N:9]([C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16])[CH2:8]2)=[O:6]>CO>[CH2:18]([O:17][C:15]([N:9]1[CH2:10][C:11]2[C:7]([C:5]([OH:6])=[O:4])([CH2:14][CH2:13][CH:12]=2)[CH2:8]1)=[O:16])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67490992HCID 67490992, compound

Product 1

HCID 67490897HCID 67490897, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 1N sodium hydroxide solution (1.86 mL) was added to a solution of {3-benzyloxycarbonyl-3-azabicyclo[3.3.0]oct-5-en-1-yl}carboxylic acid methyl ester (187 mg, 0.620 mmol) in methanol (6.20 mL) in a nitrogen atmosphere, and the mixture was stirred at room temperature for 16 hours. The reaction solution was concentrated under reduced pressure and then washed with diethyl ether (50 mL×2). The aqueous layer was made acidic with 1N hydrochloric acid under ice-cooling, followed by extraction with ethyl acetate (100 mL×1, 80 mL×1). The organic layer was washed with water (80 mL) and brine (80 mL) and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure to give 186 mg (quantitative) of the title compound.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. washwashed with diethyl ether (50 mL×2)
  3. temperaturecooling
  4. extractionfollowed by extraction with ethyl acetate (100 mL×1, 80 mL×1)
  5. washThe organic layer was washed with water (80 mL) and brine (80 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationAfter filtration
  8. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f81bd2e0f9024a2b86ed0729f8a26cfd
Source dataset
uspto-grants-2013_12
Patent number
US08618094B2

Reaction notes

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