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

HRID 1680516Notes

Reaction equation

HRID 1680516 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8].C(=O)(O)[O-].[Na+].[CH2:15]([O:22][C:23](ON1C(=O)CCC1=O)=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O.O1CCCC1>[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

6

Reactant 3

HCID 5646-Aminohexanoic AcidHCID 83172Benzyl succinimido carbonateHCID 516892Sodium Bicarbonate

Product 1

HCID 747586-(((Phenylmethoxy)carbonyl)amino)hexanoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-aminocaproic acid (7.8 g) and 5.0 g of sodium bicarbonate in 50 ml of water is added by dropwise addition 16 g of N-benzyloxycarbonyloxysuccinimide in 60 ml of tetrahydrofuran. The mixture is stirred for one hour at room temperature and then the tetrahydrofuran is removed at reduced pressure. The residue is acidified to pH 3 and extracted with methylene chloride and dried over anhydrous magnesium sulfate. The magnesium sulfate is removed by filtration and the solvent is removed by evaporation. Recrystallization from ethyl acetate/hexane provides N-benzyloxycarbonyl-6-aminocaproic acid.

Workup

  1. customthe tetrahydrofuran is removed at reduced pressure
  2. extractionextracted with methylene chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe magnesium sulfate is removed by filtration
  5. customthe solvent is removed by evaporation
  6. customRecrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-1b3b2aa06dbc45f180b5cbd2cf3087b1
Source dataset
uspto-grants-1981_06
Patent number
US04273866

Reaction notes

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