Sodium Hydroxide → 5-(((Benzyloxy)carbonyl)amino)bicyclo[3.2.1]octane-1-carboxylic acid

HRID 1408867Notes

Reaction equation

HRID 1408867 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]12[CH2:19][C:16]([C:20]([O-:22])=[O:21])([CH2:17][CH2:18]1)[CH2:15][CH2:14][CH2:13]2)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[CH2:1]([O:8][C:9]([NH:11][C:12]12[CH2:19][C:16]([C:20]([OH:22])=[O:21])([CH2:17][CH2:18]1)[CH2:15][CH2:14][CH2:13]2)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 866683955-(Benzyloxycarbonylamino)bicyclo[3.2.1]octane-1-carboxylate

Product 1

HCID 679810565-(((Benzyloxy)carbonyl)amino)bicyclo[3.2.1]octane-1-carboxylic acidYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-(benzyloxycarbonylamino)bicyclo-[3.2.1]octane-1-carboxylate (10 g, 31.5 mmol) in MeOH (150 mL) was added NaOH (2N, 50 mL) and the reaction solution was stirred at room temperature overnight. The organic solvent was removed under reduced pressure and the remaining aqueous solution was extracted with ethyl acetate (20 mL) to remove the organic impurities, and then adjusted to pH 3 with 2N aq. HCl. The acidic aqueous solution was extracted with ethyl acetate (3×20 mL) and the combined organic layer was washed with brine, dried over Na2SO4 and concentrated to give 9 g (95%) 5-(benzyloxycarbonylamino)bicyclo[3.2.1]octane-1-carboxylic acid as a colorless oil, which was solidified after standing at room temperature overnight. ESI-MS m/z: 304 (M+H)+.

Workup

  1. customThe organic solvent was removed under reduced pressure
  2. extractionthe remaining aqueous solution was extracted with ethyl acetate (20 mL)
  3. customto remove the organic impurities
  4. extractionThe acidic aqueous solution was extracted with ethyl acetate (3×20 mL)
  5. washthe combined organic layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c14271b8b5e246499254d67000032faa
Source dataset
uspto-grants-2014_12
Patent number
US08921370B2

Reaction notes

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