HCID 54132576, compound → HCID 18007271, compound

HRID 2299626Notes

Reaction equation

HRID 2299626 reaction equation
C([O:3][C:4](=[O:33])[CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]2[CH2:16][CH2:15][CH2:14][CH:13]([N:17]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:12][C:11]=2[CH:32]=1)C>C(O)C.[OH-].[Na+]>[CH2:25]([N:17]([CH:13]1[CH2:12][C:11]2[CH:32]=[C:7]([O:6][CH2:5][C:4]([OH:33])=[O:3])[CH:8]=[CH:9][C:10]=2[CH2:16][CH2:15][CH2:14]1)[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

4

Reactant 1

HCID 54132576HCID 54132576, compound

Product 1

HCID 18007271HCID 18007271, compoundYield 86.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 2-[8-(N-benzyl-N-tert-butoxycarbonyl-amino)-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-yloxy]acetic acid ethyl ester (1.6 g) in ethanol (16 ml) was added aqueous iN sodium hydroxide at 5° C., and the mixture was stirred at room temperature for 1 hour. After evaporation in vacuo, the residue was dissolved into a mixture of aqueous 0.1N hydrochloric acid and ethyl acetate. After separation, the organic layer was washed with brine, dried over anhydrous magnesium sulfate and evaporated in vacuo. The residue was triturated with hexane and dried in vacuo to give 2-[8-(N-benzyl-N-tert-butoxycarbonylamino)-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-yloxy]acetic acid (1.3 g).

Workup

  1. customAfter evaporation in vacuo
  2. dissolutionthe residue was dissolved into a mixture of aqueous 0.1N hydrochloric acid and ethyl acetate
  3. customAfter separation
  4. washthe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was triturated with hexane
  8. customdried in vacuo

Sources & evidence

ORD record
ord-94ad1cf2b44046e19b76e21e15bd91a3
Source dataset
uspto-grants-2002_12
Patent number
US06495546B1

Reaction notes

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