Z-Dehydro-Ala-OMe

Base Information

• Chemical Name: Z-Dehydro-Ala-OMe
• CAS No.: 21149-17-7
• Molecular Formula: C12H13NO4
• Molecular Weight: 235.24
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID10393314
• Nikkaji Number: J347.177B
• Wikidata: Q82192054
• Mol file: 21149-17-7.mol

Synonyms:Z-Dehydro-Ala-OMe;21149-17-7;N-Cbz-Dehydroalanine methyl ester;Methyl 2-(((benzyloxy)carbonyl)amino)acrylate;Z-Dehydroalanine methyl ester;methyl 2-(phenylmethoxycarbonylamino)prop-2-enoate;Z-Dha-OMe;MFCD00056245;2-BENZYLOXYCARBONYLAMINO-ACRYLIC ACID METHYL ESTER;methyl 2-(benzyloxycarbonylamino)acrylate;2-Propenoic acid, 2-[[(phenylmethoxy)carbonyl]amino]-, methyl ester;SCHEMBL136250;DTXSID10393314;STFUIEDYPRMRNN-UHFFFAOYSA-N;AKOS015894444;HY-W113155;AS-37167;SY007100;N-carbobenzyloxydehydroalanine methyl ester;Z-Dehydro-Ala-OMe, >=98.0% (TLC);CS-0170859;FT-0638099;Methyl2-(((benzyloxy)carbonyl)amino)acrylate;2-benzyloxycarbonylaminoacrylic acid methyl ester;A815167;A1-02629;J-013879;2-(Benzyloxycarbonylamino)propenoic acid methyl ester;Methyl 2-({[(phenylmethyl)oxy]carbonyl}amino)-2-propenoate;2-(phenylmethoxycarbonylamino)-2-propenoic acid methyl ester;2-(4-HYDROXY-PHENYL)-6-METHYL-QUINOLINE-4-CARBOXYLICACID;2-Propenoic acid,2-[[(phenylmethoxy)carbonyl]amino]-,methyl ester

Chemical Property of Z-Dehydro-Ala-OMe

Chemical Property:

• Vapor Pressure: 2.62E-05mmHg at 25°C
• Refractive Index: 1.525
• Boiling Point: 358 °C at 760 mmHg
• Flash Point: 170.3 °C
• PSA: 64.63000
• Density: 1.182 g/cm³
• LogP: 1.99040
• Storage Temp.: -15°C
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 235.08445790
• Heavy Atom Count: 17
• Complexity: 295

Purity/Quality:

99%, ^*data from raw suppliers

2-Benzyloxycarbonylamino-acrylicacidmethylester 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C(=C)NC(=O)OCC1=CC=CC=C1

Technology Process of Z-Dehydro-Ala-OMe

There total 46 articles about Z-Dehydro-Ala-OMe which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

methyl (R)-(+)-2-(benzyloxycarbonylamino)-3-chloropropionoate (62107-38-4) → methyl 2-(benzyloxycarbonylamino)acrylate (21149-17-7)

Guidance literature:

With triethylamine; In tetrachloromethane; for 18h; Ambient temperature;

Reference yield: 94.0%

Nα-(Carbobenzyloxy)-β-chloroalanine methyl ester (56618-03-2) → methyl 2-(benzyloxycarbonylamino)acrylate (21149-17-7)

Guidance literature:

With sodium methylate; In methanol; at 0 ℃; for 0.5h;

DOI:10.1016/0040-4039(91)80558-N

Reference yield: 92.0%

(S)-methyl 2-(benzyloxycarbonyl)-3-hydroxypropanoate + methanesulfonyl chloride (124-63-0) → methyl 2-(benzyloxycarbonylamino)acrylate (21149-17-7)

Guidance literature:

(S)-methyl 2-(benzyloxycarbonyl)-3-hydroxypropanoate; methanesulfonyl chloride; With triethylamine; In dichloromethane; at -15 - 0 ℃; for 0.5h;

With methanol; In dichloromethane; at 20 ℃; for 1.5h;

upstream raw materials:

diazomethane

N-benzyloxycarbonyl α-chloro glycine methyl ester

C₁₂H₁₄ClNO₄

methyl N-((benzyloxy)carbonyl)-3-iodo-L-alaninate

Downstream raw materials:

S-(2-benzyloxycarbonylamino-2-methoxycarbonyl-ethyl)-penicillamine

Z-γ,γ,-di-tert-butyl-D,L-carboxyglutamic acid methyl ester

2-benzyloxycarbonylamino-acrylic acid

2-(Benzyloxycarbonyl-methyl-amino)-acrylic acid methyl ester

Refernces

• 1、 Yamada, Masaki,Miyajima, Tadatoshi,Horikawa, Hiroshi. "Solid-phase synthesis of dehydroalanine derivatives". . p. 289 - 292. Retrieved 1998.
• 2、 Yang, Yong-Qing,Ji, Meng-Chen,Lu, Zheng,Jiang, Mao,Huang, Wei-Wei,He, Xue-Zhi. "Facile access to α,β-dehydroalanine and α,β-dehydroamino butyric acid derivatives from DL-serines and threonines". . p. 977 - 982. Retrieved 2016.
• 3、 -. "INTRANASAL PHARMACEUTICAL COMPOSITIONS OF CGRP INHIBITORS". Page/Page column 20-21; 25-26. . Retrieved 2021/06/26.
• 4、 Khan, R. Kashif M.,Zhao, Yang,Scully, Tal D.,Buchwald, Stephen L.. "Catalytic Arylhydroxylation of Dehydroalanine in Continuous Flow for Simple Access to Unnatural Amino Acids". supporting information. p. 15215 - 15218. Retrieved 2018/09/25.