Citric Acid → 4-(((Tert-butoxy)carbonyl)amino)cyclohexane-1-carboxylic acid

HRID 1861835Notes

Reaction equation

HRID 1861835 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][CH:5]([C:8]([OH:10])=[O:9])[CH2:4][CH2:3]1.[C:11](OCC)(=[O:13])C.C(O)(=O)[CH2:18][C:19]([CH2:24]C(O)=O)([C:21](O)=O)[OH:20]>[OH-].[Na+].O1CCOCC1.C(#N)C>[C:19]([O:20][C:11]([NH:1][CH:2]1[CH2:7][CH2:6][CH:5]([C:8]([OH:10])=[O:9])[CH2:4][CH2:3]1)=[O:13])([CH3:18])([CH3:21])[CH3:24]

Participants

7

Reactant 3

HCID 311Citric AcidHCID 8857Ethyl AcetateHCID 1715604-Aminocyclohexanecarboxylic acid

Product 1

HCID 27559964-(((Tert-butoxy)carbonyl)amino)cyclohexane-1-carboxylic acidYield 125%

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2.86 g (20 mmol) of 4-aminocyclohexane carboxylic acid in 40 mL of 0.5M aqueous NaOH solution, 20 mL of dioxane and 4 mL of acetonitrile was added a total of 6.5 g (30 mmol) of tBoc anhydride at room temperature. After 20 h, 100 mL of ethyl acetate and 100 mL of 10% aqueous citric acid solution were introduced. The aqueous layer which formed was separated and extracted with three-50 mL portions of ethyl acetate. The organic phases were combined, dried (sodium sulfate) and concentrated in vacuo to give 6.0 g (125%) of crude 4-(t-butoxycarbonylamino)cyclohexane carboxylic acid as a colorless oil which solidified upon standing.

Workup

  1. customThe aqueous layer which formed
  2. customwas separated
  3. extractionextracted with three-50 mL portions of ethyl acetate
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-15febe47d7d7475c8da2eb518364d168
Source dataset
uspto-grants-2003_03
Patent number
US06534531B2

Reaction notes

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