6-Aminohexanoic Acid → epsilon-(p-Azidobenzenesulfonylamino)caproic acid

HRID 1603191

Reaction equation

HRID 1603191 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8].[N:10]([C:13]1[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1)=[N+:11]=[N-:12]>C([O-])(O)=O.[Na+].O>[N:10]([C:13]1[CH:14]=[CH:15][C:16]([S:19]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8])(=[O:21])=[O:20])=[CH:17][CH:18]=1)=[N+:11]=[N-:12]

Participants

5

Reactant 2

HCID 5646-Aminohexanoic AcidHCID 5484864-Azidobenzene-1-sulfonyl chloride

Product 1

HCID 19609020epsilon-(p-Azidobenzenesulfonylamino)caproic acidYield 41.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 516892Sodium BicarbonateSolvent

Procedure

4.57 g of ε-aminocaproic acid were dissolved in a solution of 8.8 g of NaHCO3 in 100 ml water. 7.6 g of p-azidobenzenesulfonic acid chloride were suspended therein and the mixture was stirred overnight. The product was precipitated from the resulting solution with HCl, filtered off and washed with water. 4.56 g of ε-(p-azidobenzenesulfonylamino)caproic acid were obtained after drying in a high vacuum at room temperature. The IR showed the expected bands at 2907 (azide), 1715 (acid carbonyl), 1585+1400 (aromatic), 1282 (COOH), 1319+1153 (aryl sulfonyl), 834 (p- disubst. benzene); TLC (silica gel: EtOAc)/EtOH=3) Rf=0.55; m.p.=126-127° C.

Workup

  1. customThe product was precipitated from the resulting solution with HCl
  2. filtrationfiltered off
  3. washwashed with water

Sources & evidence

ORD record
ord-90550afa0d53416c841e7148df408947
Source dataset
uspto-grants-1999_11
Patent number
US05986066

Linked notes

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