116173-78-5

Basic information

• Product Name: Butanoic acid, 3-[(methoxycarbonyl)amino]-, methyl ester, (R)-
• CAS NO: 116173-78-5
• Molecular Formula: C7H13NO4
• Molecular Weight: 175.185
• Mol File: 116173-78-5.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: Butanoic acid, 3-[(methoxycarbonyl)amino]-, methyl ester, (R)-(CAS DataBase Reference)
• NIST Chemistry Reference: Butanoic acid, 3-[(methoxycarbonyl)amino]-, methyl ester, (R)-(116173-78-5)
• EPA Substance Registry System: Butanoic acid, 3-[(methoxycarbonyl)amino]-, methyl ester, (R)-(116173-78-5)

Safety Data

• Hazardous Substances Data: 116173-78-5(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 5615-90-7 3-methylsuccinimide 
• 13592-48-8 (1-methoxy-ethyl)-carbamic acid methyl ester 
• 96-32-2 bromoacetic acid methyl ester 
• 79-20-9 acetic acid methyl ester 

Downstream Products

• 61477-40-5 (R)-3-amino-1-butanol 

Relevant articles and documents

Hofmann-type rearrangement of imides by in situ generation of imide-hypervalent iodines(III) from iodoarenes

The Hofmann-type rearrangement of aromatic and aliphatic imides using a hypervalent iodine(III) reagent generated in situ from PhI, m-CPBA, and TsOH·H2O proceeded in the presence of a base in alcohol to provide anthranilic acid derivatives and amino acid derivatives in high yields, respectively. This reaction proceeds through a tandem reaction via alcoholysis followed by a Hofmann rearrangement promoted by the formation of an imide-λ3-iodane intermediate.

A new method for the synthesis of β-amino acid derivatives and β- lactams. Reaction of N-alkoxycarbonyl-1-methoxyamines with esters

The reaction of N-alkoxycarbonyl-1-methoxyamines with esters is an alternative to the reaction of imines with esters for the synthesis of β- amino acid derivatives. In this reaction, N-alkoxycarbonyl-1-methoxyamines corresponding to unstable imines can also be employed. Although anti adducts were obtained preferentially in the absence of Ti complexes, the diastereoselectivity of this reaction was reversed by the addition of Ti(OPr- i)4. The obtained adducts were transformed to the corresponding β-lactams.

NEW SYNTHESIS OF β-AMINO ACIDS BY NUCLEOPHILIC ADDITION OF ENOLATE ANIONS TO N-METHOXYCARBONYLIMINES GENERATED FROM α-METHOXY CARBAMATES.

The nucleophilic addition of enolate anions of alkyl acetates to N-methoxycarbonylimines generated from α-methoxy carbamates gave β-amino acid derivates (3) and enantioselective synthesis (72-90percentee) of 3 was achieved by using chiral 2-methyloxazolines instead of acetates.