198217-06-0

Basic information

• Product Name: N^α-benzoyloxy-3-(tert-butoxycarbonylamino)propylamine
• Synonyms: N^α-benzoyloxy-3-(tert-butoxycarbonylamino)propylamine
• CAS NO: 198217-06-0
• Molecular Weight: 294.351
• Mol File: 198217-06-0.mol

Chemical Properties

• CAS DataBase Reference: N^α-benzoyloxy-3-(tert-butoxycarbonylamino)propylamine(CAS DataBase Reference)
• NIST Chemistry Reference: N^α-benzoyloxy-3-(tert-butoxycarbonylamino)propylamine(198217-06-0)
• EPA Substance Registry System: N^α-benzoyloxy-3-(tert-butoxycarbonylamino)propylamine(198217-06-0)

Safety Data

• Hazardous Substances Data: 198217-06-0(Hazardous Substances Data)

Upstream product

• 75178-96-0 N-Boc-1,3-diaminopropane 
• 94-36-0 dibenzoyl peroxide 
• 24424-99-5 di-tert-butyl dicarbonate 
• 93-59-4 Perbenzoic acid 

Downstream Products

• 198217-02-6 {3-[Benzoyloxy-((E)-oct-2-enoyl)-amino]-propyl}-carbamic acid tert-butyl ester 
• 1392827-20-1 tert-butyl (3-(2-phenylacetamido)propyl)carbamate 
• 778591-27-8 2-tert-butyl-1,3-((3-N-benzoyloxy-3-N-(2-trans-dodecenoyl))propyl)diamide citrate 
• 778591-25-6 2-tert-butyl-1,3-((3-N-benzoyloxy-3-N-(2-trans-octenoyl))propyl)diamide citrate 
• 778591-26-7 2-tert-butyl-1,3-((3-N-benzoyloxy-3-N-crotonyl)propyl)diamide citrate 
• 778591-24-5 2-tert-butyl-1,3-((3-N-benzoyloxy-3-N-acetyl)propyl)diamide citrate 
• 778591-23-4 tert-butyl 4-((3-((benzoyloxy)amino)propyl)amino)-2-(2-((3-((benzoyloxy)amino)propyl)amino)-2-oxoethyl)-2-hydroxy-4-oxobutanoate 
• 864531-12-4 N-[3-(benzoyloxy-octadec-2-enoyl-amino)-propyl]-2-{[3-(benzoyloxy-octadec-2-enoyl-amino)-propylcarbamoyl]-methyl}-2-hydroxy-succinamic acid tert-butyl ester 
• 864531-06-6 N-(3-{benzoyloxy-[3-(4-trifluoromethyl-phenyl)-acryloyl]-amino}-propyl)-2-[(3-{benzoyloxy-[3-(4-trifluoromethyl-phenyl)-acryloyl]-amino}-propylcarbamoyl)-methyl]-2-hydroxy-succinamic acid tert-butyl ester 
• 864531-10-2 N-[3-(benzoyloxy-octanoyl-amino)-propyl]-2-{[3-(benzoyloxy-octanoyl-amino)-propylcarbamoyl]-methyl}-2-hydroxy-succinamic acid tert-butyl ester 
• 864531-08-8 [3-(N-acetyl-N-benzoyloxyamino)propyl]carbamic acid tert-butyl ester 

Relevant articles and documents

Total synthesis of acinetoferrin

The total synthesis of a novel siderophore, acinetoferrin, is described. The key transformation involves the tandem oxidation and acylation of the N3-amino group of N1-BOC propane diamine prior to coupling with the external carboxyls of citric acid. A 'one-pot-two-step' reaction converted a primary amine (RNH2) into a O-benzoyl hydroxamate (i.e., RN(OOCPh)COR') in good yield (68%). These studies demonstrated the utility of the O-benzoyl protecting group in the synthesis of α,β-unsaturated hydroxamic acids.

An Improved Synthesis of O-Benzoyl Protected Hydroxamates

Several primary amines (R-NH2) were converted to their corresponding O-benzoyl protected hydroxamates under biphasic conditions. The intermediate (benzoyloxy)amines (R-NHOCOPh) were generated using benzoyl peroxide dissolved in CH2Cl2 and an aqueous carbonate buffer (pH 10.5) at room temperature. Subsequent acylation with R'COCl gave the protected hydroxamates (R'CONROCOPh) in good overall yields (56-89%).

Synthesis of secondary amines via N-(benzoyloxy)amines and organoboranes

A variety of primary amines (R-NH2) were converted to their corresponding N-(benzoyloxy)amines (i.e., R-NHOCOPh) under biphasic conditions in excellent yields (63-90%). The intermediate N- (benzoyloxy)amines were converted to their N-ethylamine derivatives upon reaction with triethylborane in THF in good yield (54-89%). These experiments demonstrated the similar chemistry of N-chloro- and N-(benzoyloxy)amines with organoboranes.