156706-51-3

Basic information

• Product Name: Carbamic acid, [(1S)-2-(hydroxyamino)-1-methyl-2-oxoethyl]-, 1,1-
• Synonyms: Carbamic acid, [(1S)-2-(hydroxyamino)-1-methyl-2-oxoethyl]-, 1,1-
• CAS NO: 156706-51-3
• Molecular Formula: C₈H₁₆N₂O₄
• Molecular Weight: 204.22364
• Product Categories: N-BOC
• Mol File: 156706-51-3.mol
• Article Data: 11

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Carbamic acid, [(1S)-2-(hydroxyamino)-1-methyl-2-oxoethyl]-, 1,1-(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, [(1S)-2-(hydroxyamino)-1-methyl-2-oxoethyl]-, 1,1-(156706-51-3)
• EPA Substance Registry System: Carbamic acid, [(1S)-2-(hydroxyamino)-1-methyl-2-oxoethyl]-, 1,1-(156706-51-3)

Safety Data

• Hazardous Substances Data: 156706-51-3(Hazardous Substances Data)

Upstream product

• 28875-17-4 (S)-N-(tert-butoxycarbonyl)alanine methyl ester 
• 15761-38-3 L-N-Boc-Ala 
• 39982-01-9 tert-Butoxycarbonylpivalat 
• 631914-55-1 Boc-L-Ala-Cl 
• 24424-99-5 di-tert-butyl dicarbonate 

Downstream Products

• 160057-21-6 1(R)-1-<(tert-Butyldiphenylsilyl)oxy>-4(S)-cyclopent-2-ene 
• 160057-23-8 {(S)-1-[(1S,2R,3R,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-2,3-dihydroxy-cyclopentylcarbamoyl]-ethyl}-carbamic acid tert-butyl ester 
• 160057-25-0 {(S)-1-[(3aR,4S,6R,6aR)-6-(tert-Butyl-diphenyl-silanyloxy)-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-ylcarbamoyl]-ethyl}-carbamic acid tert-butyl ester 

Relevant articles and documents

Organocatalytic Multicomponent Synthesis of α/β-Dipeptide Derivatives

A straightforward multicomponent Knoevenagel-aza-Michael-cyclocondensation reaction involving readily available hydroxamic acid-derived from naturally occurring α-amino acids allows a diversity-oriented synthesis of novel isoxazolidin-5-ones possessing an N-protected α-amino acid pendant with good to high diastereoselectivities thanks to a match effect with a chiral organocatalyst. These diversely substituted heterocycles, easily isolated as a single diastereoisomer, proved to be versatile platforms for the formation of an array of α/β-dipeptide fragments.

Effective synthesis of enantiopure hydroxamates by displacement of resin-bound esters with hydroxylamine

Enantiopure hydroxamic acids have been synthesized by nucleophilic displacement of carboxylates linked to oxime resin using hydroxylamine in a MeOH:CHCl3 solution.

The synthesis of Nα-protected amino hydroxamic acids from Nα-protected amino acids employing versatile chlorinating agent CPI-Cl

Racemization free synthesis of Nα-protected amino hydroxamic acids from Nα-protected amino acids employing the versatile chlorinating reagent CPI-Cl has been described in one-pot. The present protocol has shown compability towards urethane protecting groups like Boc, Cbz and Fmoc, and side chain protections of amino acids showed complete tolerance.

Efficient continuous flow synthesis of hydroxamic acids and suberoylanilide hydroxamic acid preparation

A continuous flow tubing reactor can be used to readily transform methyl or ethyl carboxylic esters into the corresponding hydroxamic acids. Flow rate, reactor volume, and temperature were optimized for the preparation of a small collection of hydroxamic acids. Synthetic advantages were identified as an increased reaction rate and higher product purity. This method was also successfully applied to the multistep preparation of suberoylanilide hydroxamic acid, a potent HDAC inhibitor used in anticancer therapy.