Hydrochloric Acid → 6-(Tert-butoxycarbonylamino)norbornane-2-carboxylic acid

HRID 75047Notes

Reaction equation

HRID 75047 reaction equation
[C:1]([O:5][C:6]([N:8](C(=O)C(OCC)=O)[CH:9]1[CH:14]2[CH2:15][CH:11]([CH2:12][CH:13]2[C:16]([O:18]C)=[O:17])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl>CO>[C:1]([O:5][C:6]([NH:8][CH:9]1[CH:14]2[CH2:15][CH:11]([CH2:12][CH:13]2[C:16]([OH:18])=[O:17])[CH2:10]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67286117Methyl 6-[tert-butoxycarbonyl-(2-ethoxy-2-oxo-acetyl)amino]norbornane-2-carboxylate

Product 1

HCID 672859386-(Tert-butoxycarbonylamino)norbornane-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 6-[tert-butoxycarbonyl-(2-ethoxy-2-oxo-acetyl)amino]norbornane-2-carboxylate, 72f, (0.80 g, 2.17 mmol) in methanol (20 mL) was added NaOH (4.33 mL of 2N solution, 8.66 mmol) at room temperature. The reaction mixture was stirred overnight. The mixture was diluted into 0.5 N HCl in ice, and extracted twice with EtOAc. The combined organic phases were dried (Na2SO4), filtered and concentrated in vacuo to afford 600 mg of desired product that was used without further purification.

Workup

  1. extractionextracted twice with EtOAc
  2. dry with materialThe combined organic phases were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-906f4ef20f494d3b8c72e92acece46e4
Source dataset
uspto-grants-2014_09
Patent number
US08829007B2

Reaction notes

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