Methyl 2-((tert-butoxycarbonyl)amino)pent-4-enoate

Base Information

• Chemical Name: Methyl 2-((tert-butoxycarbonyl)amino)pent-4-enoate
• CAS No.: 106928-50-1
• Molecular Formula: C11H19NO4
• Molecular Weight: 229.276
• DSSTox Substance ID: DTXSID70446113
• Nikkaji Number: J994.005G
• Mol file: 106928-50-1.mol

Synonyms:Methyl 2-((tert-butoxycarbonyl)amino)pent-4-enoate;106928-50-1;Methyl 2-[(2-methylpropan-2-yl)oxycarbonylamino]pent-4-enoate;methyl 2-[(tert-butoxycarbonyl)amino]pent-4-enoate;MFCD13190790;2-tert-butoxycarbonylamino-pent-4-enoic acid methyl ester;(2R)-2-(Boc-amino)-4-pentenoic acid methyl ester;SCHEMBL614514;DTXSID70446113;APXWRHACXBILLH-UHFFFAOYSA-N;Methyl-2-Boc-AMino-4-pentenoic acid;AKOS016003175;AB86816;PB43789;Methyl (S)-2-(Boc-amino)-4-pentenoate;SY127260;CS-0267233;2-(Boc-amino)-4-pentenoic acid methyl ester;F14155;EN300-6201470;Methyl2-((tert-butoxycarbonyl)amino)pent-4-enoate;methyl 2-{[(tert-butoxy)carbonyl]amino}pent-4-enoate;methyl (2S)-2-(tert-butoxycarbonylamino)pent-4-enoate;2-(tert-Butoxycarbonylamino)-4-pentenoic acid methyl ester;methyl2-[((1,1-dimethylethoxy)carbonyl)amino]-4-pentenoate

Chemical Property of Methyl 2-((tert-butoxycarbonyl)amino)pent-4-enoate

Chemical Property:

• Storage Temp.: 2-8°C
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 229.13140809
• Heavy Atom Count: 16
• Complexity: 268

Purity/Quality:

99%+, ^*data from raw suppliers

Methyl2-((tert-butoxycarbonyl)amino)pent-4-enoate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CC=C)C(=O)OC

Technology Process of Methyl 2-((tert-butoxycarbonyl)amino)pent-4-enoate

There total 17 articles about Methyl 2-((tert-butoxycarbonyl)amino)pent-4-enoate 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: 99.0%

allyl bromide (106-95-6) + acetyloxy[[(1,1-dimethylethoxy)carbonyl]amino]acetic acid methyl ester (173306-81-5) → methyl 2-[(tert-butoxycarbonyl)amino]pent-4-enoate (106928-50-1)

Guidance literature:

With zinc; In N,N-dimethyl-formamide; at 20 - 25 ℃;

DOI:10.1016/S0040-4039(00)73067-X

Reference yield: 94.0%

2-((tert-butyloxycarbonyl)amino)-4-pentenoic acid (119479-32-2) + methyl iodide (74-88-4) → methyl 2-[(tert-butoxycarbonyl)amino]pent-4-enoate (106928-50-1)

Guidance literature:

2-((tert-butyloxycarbonyl)amino)-4-pentenoic acid; With potassium carbonate; In DMF (N,N-dimethyl-formamide); for 0.25h;

methyl iodide; In DMF (N,N-dimethyl-formamide); at 0 - 20 ℃; for 4h;

Reference yield: 94.0%

di-tert-butyl dicarbonate (24424-99-5) + methyl iodide (74-88-4) → methyl 2-[(tert-butoxycarbonyl)amino]pent-4-enoate (106928-50-1)

Guidance literature:

rac-allylglycine; di-tert-butyl dicarbonate; With sodium hydroxide; In 1,4-dioxane; water; at 0 ℃; for 16h;

With hydrogenchloride; In 1,4-dioxane; water; pH=2;

methyl iodide; With potassium carbonate; more than 3 stages;

upstream raw materials:

diazomethane

2-((tert-butyloxycarbonyl)amino)-4-pentenoic acid

di-tert-butyl dicarbonate

allyl bromide

Downstream raw materials:

(E)-1,2-diphenyl-ethene

5-(4-bromophenyl)-2-tert-butoxycarbonylamino-4-pentenoic acid methyl ester

methyl (S)-allylglycinate

2-((tert-butyloxycarbonyl)amino)-4-pentenoic acid

Refernces

• 1、 Abood, Norman A.,Nosal, Roger. "Zinc mediated addition of active halides to a glycine cation equivalent: Synthesis of N-Boc-L-propargylglycine". . p. 3669 - 3672. Retrieved 1994.
• 2、 -. "3,5-DIAMINO-6-CHLORO-PYRAZINE-2-CARBOXYLIC ACID DERIVATIVES AND THEIR USE AS EPITHELIAL SODIUM CHANNEL BLOCKERS FOR THE TREATMENT OF ARWAY DISEASES". Page/Page column 43. . Retrieved 2009/12/23.