Methyl 2-((tert-butoxycarbonyl)amino)but-3-enoate

Base Information

• Chemical Name: Methyl 2-((tert-butoxycarbonyl)amino)but-3-enoate
• CAS No.: 100038-68-4
• Molecular Formula: C10H17NO4
• Molecular Weight: 215.249
• European Community (EC) Number: 869-808-6
• Nikkaji Number: J1.323.331D
• Mol file: 100038-68-4.mol

Synonyms:100038-68-4;methyl 2-((tert-butoxycarbonyl)amino)but-3-enoate;methyl 2-[(2-methylpropan-2-yl)oxycarbonylamino]but-3-enoate;SCHEMBL19056015;AT29162;EN300-6213525;methyl2-((tert-butoxycarbonyl)amino)but-3-enoate;methyl 2-{[(tert-butoxy)carbonyl]amino}but-3-enoate;2-[(tert-Butyloxycarbonyl)amino]-3-butenoic acid methyl ester

Chemical Property of Methyl 2-((tert-butoxycarbonyl)amino)but-3-enoate

Chemical Property:

• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 215.11575802
• Heavy Atom Count: 15
• Complexity: 255

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

Technology Process of Methyl 2-((tert-butoxycarbonyl)amino)but-3-enoate

There total 8 articles about Methyl 2-((tert-butoxycarbonyl)amino)but-3-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: 88.0%

(Z)-methyl 2-((tertbutoxycarbonyl)amino)but-2-enoate (63658-16-2) → 2-tert-Butoxycarbonylamino-but-3-enoic acid methyl ester (100038-68-4,852693-74-4)

Guidance literature:

With dibromo(dimethylglyoxime)(dimethylglyoximato)cobalt(III); sodium decatungstate; 1,2-bis(2,4,6-triisopropylphenyl)disulfane; In acetone; at 20 ℃; for 18h; regiospecific reaction; Irradiation; Inert atmosphere; Sealed tube;

DOI:10.1021/jacs.1c12043

Reference yield: 20.0%

vinyl magnesium bromide (1826-67-1) + 2-bromo-2-(N-tert-butoxycarbonylamino)acetic acid methyl ester (138219-39-3) → 2-tert-Butoxycarbonylamino-but-3-enoic acid methyl ester (100038-68-4,852693-74-4)

Guidance literature:

In tetrahydrofuran; at -78 ℃; for 2h;

Reference yield:

N-(tert-butoxycarbonyl)glycine methyl ester (31954-27-5) → 2-tert-Butoxycarbonylamino-but-3-enoic acid methyl ester (100038-68-4,852693-74-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / NBS / dimethylsulfoxide / 1 h / 10 - 30 °C / Irradiation

2: 20 percent / tetrahydrofuran / 2 h / -78 °C

With N-Bromosuccinimide; In tetrahydrofuran; dimethyl sulfoxide;

upstream raw materials:

N-(tert-butoxycarbonyl)-L-methionine methyl ester

tert-butyl carbazate

methyl 4-(phenylseleno)-2(E)-butenoate

vinyl magnesium bromide

Downstream raw materials:

2-amino-3-butenoic acid

Refernces

• 1、 Biagini, Stefano C. G.,Gibson, Susan E.,Keen, Stephen P.. "Cross-metathesis of unsaturated α-amino acid derivatives". . p. 2485 - 2499. Retrieved 2007/10/03.
• 2、 Fitzner, Jeffrey N.,Pratt, Daniel V.,Hopkins, Paul B.. "Synthesis of Protected Racemic β,γ-Unsaturated-α-Amino Acids via γ-Phenylseleno-α,β-Unsaturated Esters". . p. 1959 - 1962. Retrieved 2007/10/02.