83460-84-8

Basic information

• Product Name: Butanoic acid, 3-[[(phenylmethoxy)carbonyl]amino]-, methyl ester, (3S)-
• CAS NO: 83460-84-8
• Molecular Formula: C13H17NO4
• Molecular Weight: 251.282
• Mol File: 83460-84-8.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: Butanoic acid, 3-[[(phenylmethoxy)carbonyl]amino]-, methyl ester, (3S)-(CAS DataBase Reference)
• NIST Chemistry Reference: Butanoic acid, 3-[[(phenylmethoxy)carbonyl]amino]-, methyl ester, (3S)-(83460-84-8)
• EPA Substance Registry System: Butanoic acid, 3-[[(phenylmethoxy)carbonyl]amino]-, methyl ester, (3S)-(83460-84-8)

Safety Data

• Hazardous Substances Data: 83460-84-8(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 501-53-1 benzyl chloroformate 
• 5303-65-1 (S)-ethyl 3-aminobutyrate 
• 105-45-3 acetoacetic acid methyl ester 
• 67-63-0 isopropyl alcohol 
• 121054-27-1 Methyl (+/-)-3-<(benzyloxycarbonyl)amino>butanoate 
• 100-51-6 benzyl alcohol 
• 426254-23-1 (-)-tert-butyl (S)-N-(benzyloxycarbonyl)-3-aminobutanoate 
• 1142-20-7 N-Cbz-Ala 
• 621-84-1 O-benzyl carbamate 
• 6078-06-4 (S)-methyl 3-aminobutanoate 
• 67865-68-3 benzyl (S)-(4-diazo-3-oxobutan-2-yl)carbamate 

Downstream Products

• 1352133-58-4 methyl (2S,3S)-3-(benzyloxycarbonylamino)-2-fluorobutanoate 
• 83509-91-5 (S)-3-[(S)-3-((S)-3-Benzyloxycarbonylamino-butyrylamino)-butyrylamino]-butyric acid methyl ester 
• 83509-90-4 (S)-3-Benzyloxycarbonylamino-butyric acid 2,4,5-trichloro-phenyl ester 
• 83460-92-8 (S)-3-((S)-3-Benzyloxycarbonylamino-butyrylamino)-butyric acid methyl ester 
• 83460-93-9 (S)-3-((S)-3-Benzyloxycarbonylamino-butyrylamino)-butyric acid 
• 83460-94-0 (S)-3-((S)-3-Benzyloxycarbonylamino-butyrylamino)-butyric acid 2,4,5-trichloro-phenyl ester 
• 83460-76-8 (S)-3-[(S)-3-((S)-3-Benzyloxycarbonylamino-butyrylamino)-butyrylamino]-butyric acid 
• 113034-32-5 methyl ester of (S)-3-(benzoylamino)butanoic acid 
• 161010-99-7 benzyl (1S)-1-[(3S)-1-benzyl-2-oxopyrrolidin-3-yl]ethylcarbamate 
• 161011-00-3 N-{(1S)-1-[(3R)-1-benzylpyrrolidin-3-yl]ethyl}-N-methylamine 
• 175225-31-7 methyl (2S)-2-((1S)-1-{[(benzyloxy)carbonyl]amino}ethyl)pent-4-enoate 
• 6078-06-4 (S)-methyl 3-aminobutanoate 
• 83509-88-0 (S)-3-benzyloxycarbonylaminobutyric acid 

Relevant articles and documents

Synthesis of chiral non-racemic intermediates and Arg-Gly-Asp mimetics by CaLB-catalyzed resolution

The reactivity of both the ester and amine functions present in β-amino esters was tested in order to obtain the synthesis of enantiopure αvβ3 and α5β1 integrin ligands. CaLB successfully catalyzed both the enantioselective transesterification and the N-acylation of racemic β-amino esters, allowing the isolation of intermediates for the preparation of Arg-Gly-Asp (RGD) mimetic compounds. In particular, a CaLB-catalyzed amidation reaction with unprotected p-aminobenzylamine reduced the number of synthetic steps, thus avoiding protection and deprotection of the intermediate compounds. Following this procedure, RGD mimetics were isolated with high yields and enantiomeric purities.

One-pot hydrogenation conditions for a sequential process to (+)-monomorine

(+)-Monomorine has been synthesized under mild hydrogenation conditions initiating deprotection followed by intramolecular, sequential reductive amination reactions. The precursors could be prepared concisely using B-alkyl Suzuki cross coupling of a chiral homoallylamine and a vinyl iodide or an iodofuran derivative.

Synthesis of N-Methyl-N-{(1S)-1-[(3R)-pyrrolidin-3-yl]ethyl} amine

N-Methyl-N-{(1S)-1-[(3R)-pyrrolidin-3-yl]ethyl} amine (1)1 is a key intermediate in the preparation of premafloxacin (2), which was under development as an antibiotic for use against pathogens of veterinary importance. This paper describes the development of a practical, efficient, and stereoselective process for the preparation of 1 from isobutyl (3S)-3-{methyl[(1S)-1-phenylethyl]-amino}butanoate (5c). The key steps in the synthetic sequence are an asymmetric Michael addition, which yields 5c, and a stereoselective alkylation, which yields (3S,4S)-3-allyl-1,4-dimethylazetidin-2-one (17).