6-Aminohexanoic Acid → 6-(((Phenylmethoxy)carbonyl)amino)hexanoic acid

HRID 1756250Notes

Reaction equation

HRID 1756250 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8].Cl[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12]>O.[OH-].[Na+]>[CH2:14]([O:13][C:11]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8])=[O:12])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 5646-Aminohexanoic AcidHCID 10387Benzyl chloroformate

Product 1

HCID 747586-(((Phenylmethoxy)carbonyl)amino)hexanoic acidYield 83%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent2×

Procedure

The first step was to protect 6-aminocaproic acid using benzyl chloroformate to give N-benzyloxycarbonyl-6-aminocaproic acid. This first step was carried out as follows. A solution of 6-aminocaproic acid (32.8 g, 0.25M) in 75 mL of H2O and 42 mL of 6N NaOH was cooled in a salt-ice bath to below 10° C. With stirring, benzyl chloroformate, 46.9 g, 0.275M) and 2N NaOH (138 mL) were alternatively added in small portions over 90 min. After the addition was complete, the solution was brought to room temperature, and stirring was continued for an additional 1 hr. The product was precipitated by lowering the pH to 2 with concentrated HCL, and H2O was added as required to keep the suspension stirring. The white precipitate was filtered, then resuspended and triturated with 1 liter of water. The solid was filtered, washed with water, compressed and then washed with hexane. The solid was then thoroughly dried in a vacuum desiccator to yield 55 grams (83% yield) of N-benzyloxycarbonyl-6-aminocaproic acid.

Workup

  1. additionAfter the addition
  2. customwas brought to room temperature
  3. stirringstirring
  4. customThe product was precipitated
  5. additionwas added
  6. stirringstirring
  7. filtrationThe white precipitate was filtered
  8. customtriturated with 1 liter of water
  9. filtrationThe solid was filtered
  10. washwashed with water
  11. washwashed with hexane
  12. customThe solid was then thoroughly dried in a vacuum desiccator

Sources & evidence

ORD record
ord-ebe1f54138a34ab5bdc5f90dd15658da
Source dataset
uspto-grants-1995_08
Patent number
US05440023

Reaction notes

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