56762-93-7

Basic information

• Product Name: Z-L-METHIONINE METHYL ESTER
• Synonyms: Z-MET-OME;Z-L-METHIONINE METHYL ESTER;CBZ-L-METHIONINE METHYL ESTER;N-Benzyloxycarbonyl-L-methionine methyl ester;AC-Gly-Gly;L-Cbz methionine methyl ester;(S)-2-[(Benzyloxycarbonyl)amino]-4-methylsulfanylbutanoic acid methyl ester;-Methyl 2-(((benzyloxy)
• CAS NO: 56762-93-7
• Molecular Formula: C₁₄H₁₉NO₄S
• Molecular Weight: 297.37
• Mol File: 56762-93-7.mol
• Article Data: 21

Chemical Properties

• Melting Point: 41-44 °C
• Boiling Point: 453.622 °C at 760 mmHg
• Flash Point: 228.142 °C
• Appearance: /
• Density: 1.183 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.538
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 10.77±0.46(Predicted)
• CAS DataBase Reference: Z-L-METHIONINE METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: Z-L-METHIONINE METHYL ESTER(56762-93-7)
• EPA Substance Registry System: Z-L-METHIONINE METHYL ESTER(56762-93-7)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 56762-93-7(Hazardous Substances Data)

Usage

Uses

Intermediate for the synthesis of derivatives of L-vinylglycine [(S)-2-amino-3-butenoic acid.

InChI:InChI=1/C14H19NO4S/c1-18-13(16)12(8-9-20-2)15-14(17)19-10-11-6-4-3-5-7-11/h3-7,12H,8-10H2,1-2H3,(H,15,17)/t12-/m0/s1

Upstream product

• 110761-07-4 N-(tert-butyldimethylsilyloxycarbonyl)-L-methionine methyl ester 
• 100-39-0 benzyl bromide 
• 67-56-1 methanol 
• 63-68-3 L-methionine 
• 501-53-1 benzyl chloroformate 
• 75266-39-6 methyl (S)-2-<<(benzyloxy)carbonyl>amino>-4-(methylsulfinyl)butanoate 
• 115481-99-7 (S)-3-benzyloxycarbonyl-4-(2-methylthioethyl)oxazolidin-5-one 
• 127862-75-3 2-Benzyloxycarbonylamino-4-methylsulfanyl-butyric acid 2,2,2-trifluoro-ethyl ester 
• 33900-24-2 t-BOC-L-Met-OMe 
• 42417-81-2 (2S)-2-(methyl{[(phenylmethyl)oxy]carbonyl}amino)-4-(methylsulfanyl)butanoic acid 
• 13139-17-8 N-(Benzyloxycarbonyloxy)succinimide 
• 2491-18-1 (S)-methyl 2-amino-4-(methylthio)butanoate hydrochloride 
• 429-41-4 tetrabutyl ammonium fluoride 
• 33900-24-2 N-(tert-butoxycarbonyl)-L-methionine methyl ester 

Downstream Products

• 15998-52-4 Z-Met-NH₂ 
• 3561-51-1 benzyl (S)-(1-hydrazinyl-4-(methylthio)-1-oxobutan-2-yl)carbamate 
• 478647-31-3 tert-butyl N-[(benzyloxy)carbonyl]-L-methionyl-L-alaninate 
• 151929-39-4 ethyl (4S)-4-(benzyloxycarbonylamino)-6-methylthio-2-hexenoate 
• 72015-57-7 (Z)-2-(benzyloxycarbonylamino)but-2-enoic acid 
• 2483-62-7 (S)-2-aminobutyric acid methyl ester 
• 70363-18-7 N-<1-(Methoxycarbonyl)propyl>-α-methoxy-α-<(trifluoromethyl)phenyl>acetamide 
• 142698-79-1 methyl (2S,3R)-2-<(benzyloxy)carbonylamino>-4-chloro-3-hydroxybutanoate 
• 142698-78-0 methyl (2S,3S)-2-<(benzyloxy)carbonylamino>-4-chloro-3-hydroxybutanoate 
• 117751-78-7 Methyl (2S,3R)-2-<<(benzyloxy)carbonyl>amino>-3,4-epoxybutanoate 
• 117751-79-8 Methyl (2S,3S)-2-<<(benzyloxy)carbonyl>amino>-3,4-epoxybutanoate 
• 117751-72-1 methyl (2S,3R)-3-acetoxy-2-(benzyloxycarbonyl)aminobutanoate 
• 117751-88-9 O-acetyl-N-benzyloxycarbonyl-L-allothreonine methyl ester 
• 117751-87-8 (2S,3R)-2-Benzyloxycarbonylamino-4-bromo-3-hydroxy-butyric acid methyl ester 

Relevant articles and documents

An improved protocol for the preparation of (S)-vinylglycine from (S)-methionine

We present an optimized procedure for the synthesis of (S)-vinylglycine from (S)-methionine. The key step is a solvent free pyrolysis of an intermediate sulfoxide at high temperature. Using our optimized reaction conditions, Cbz-protected vinylglycine was

Electrophilic Chlorine from Chlorosulfonium Salts: A Highly Chemoselective Reduction of Sulfoxides

Herein, we describe a selective late-stage deoxygenation of sulfoxides based on a novel application of chlorosulfonium salts and demonstrate a new process using these species generated in situ from sulfoxides as the source of electrophilic chlorine. The use of highly nucleophilic 1,3,5-trimethoxybenzene (TMB) as the reducing agent is described for the first time and applied in the deoxygenation of simple and functionalized sulfoxides. The method is easy to handle, economic, suitable for gram-scale operations, and readily applied for poly-functionalized molecules, as demonstrated with more than 45 examples, including commercial medicines and analogues. We also report the results of competition experiments that define the more reactive sulfoxide and we present a mechanistic proposal based on substrate and product observations.

Amidation of unactivated ester derivatives mediated by trifluoroethanol

A catalytic amidation protocol mediated by 2,2,2-trifluoroethanol has been developed, facilitating the condensation of unactivated esters and amines, furnishing both secondary and tertiary amides. The complete scope and limitations of the method are described, along with modified conditions for challenging substrates such as acyclic secondary amines and chiral esters with retention of chiral integrity.