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

HRID 462901Notes

Reaction equation

HRID 462901 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8].C(OCC)C.[CH2:15]([O:22][C:23](Cl)=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>[OH-].[Na+]>[CH2:15]([O:22][C:23]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8])=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 5646-Aminohexanoic AcidHCID 3283Diethyl EtherHCID 10387Benzyl chloroformate

Product 1

HCID 747586-(((Phenylmethoxy)carbonyl)amino)hexanoic acidYield 92%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent2×

Procedure

To a solution of 6.56 g (50 mmoles) of 6-aminohexanoic acid in 25 ml of 2N aqueous sodium hydroxide solution was added 5 ml of ethyl ether. To the mixture, while being cooled in ice and stirred, were added dropwise over a period of 30 minutes 10 ml of benzyloxycarbonyl chloride and 37.5 ml of 2N aqueous sodium hydroxide solution. After the addition, the temperature was brought back to room temperature and the stirring was continued for 2 hours. The reaction mixture was washed twice with 20 ml of ethyl ether. The aqueous layer was acidified with concentrated hydrochloric acid and extracted 3 times with 50 ml of ethyl acetate. The extract solutions were combined, washed with saturated saline, dried over anhydrous sodium sulfate and freed from the solvent by distillation to obtain 12.16 g (92% yield) of 6-benzyloxycarbonylaminohexanoic acid with a melting point of 127°-128° C.

Workup

  1. temperatureTo the mixture, while being cooled in ice
  2. additionAfter the addition
  3. customwas brought back to room temperature
  4. washThe reaction mixture was washed twice with 20 ml of ethyl ether
  5. extractionextracted 3 times with 50 ml of ethyl acetate
  6. washwashed with saturated saline
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationfreed from the solvent by distillation

Sources & evidence

ORD record
ord-ca50f3ee00f441ab96640c2f3aef7272
Source dataset
uspto-grants-1985_05
Patent number
US04518532

Reaction notes

Loading…