2-Methyl-4-[(tert-butoxycarbonyl)amino]-2-butenoic acid

Base Information

• Chemical Name: 2-Methyl-4-[(tert-butoxycarbonyl)amino]-2-butenoic acid
• CAS No.: 128121-02-8
• Molecular Formula: C₁₀H₁₇NO₄
• Molecular Weight: 215.249
• European Community (EC) Number: 960-635-2
• Nikkaji Number: J1.511.318I
• Mol file: 128121-02-8.mol

Synonyms:128121-02-8;2-Methyl-4-[(tert-butoxycarbonyl)amino]-2-butenoic acid;4-{[(tert-butoxy)carbonyl]amino}-2-methylbut-2-enoic acid;(E)-2-methyl-4-[(2-methylpropan-2-yl)oxycarbonylamino]but-2-enoic acid;EN300-304611;EN300-1428796;4-{[(tert-butoxy)carbonyl]amino}-2-methylbut-2-enoicacid;(2E)-4-{[(tert-butoxy)carbonyl]amino}-2-methylbut-2-enoic acid;2102890-32-2

Chemical Property of 2-Methyl-4-[(tert-butoxycarbonyl)amino]-2-butenoic acid

Chemical Property:

• XLogP3: 1.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 215.11575802
• Heavy Atom Count: 15
• Complexity: 276

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=CCNC(=O)OC(C)(C)C)C(=O)O
• Isomeric SMILES: C/C(=C\CNC(=O)OC(C)(C)C)/C(=O)O

Technology Process of 2-Methyl-4-[(tert-butoxycarbonyl)amino]-2-butenoic acid

There total 2 articles about 2-Methyl-4-[(tert-butoxycarbonyl)amino]-2-butenoic acid 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:

2-(diethylphosphono)propionic acid (30094-28-1) + N-(t-butoxycarbonyl)glycinal (89711-08-0) → (trans)-4-[(t-butoxycarbonyl)amino]-2-methyl-2-butenoic acid (128121-02-8) + (cis)-4-[(t-butoxycarbonyl)amino]-2-methyl-2-butenoic acid (356788-94-8)

Guidance literature:

2-(diethylphosphono)propionic acid; With n-butyllithium; In tetrahydrofuran; at -60 ℃; for 0.5h;

N-(t-butoxycarbonyl)glycinal; In tetrahydrofuran; at -60 - 25 ℃; for 4h;

DOI:10.1016/S0040-4020(01)00433-1

Reference yield:

ethyl 2-diethoxyphosphorylpropionate (3699-66-9) + N-(t-butoxycarbonyl)glycinal (89711-08-0) → (trans)-4-[(t-butoxycarbonyl)amino]-2-methyl-2-butenoic acid (128121-02-8) + (cis)-4-[(t-butoxycarbonyl)amino]-2-methyl-2-butenoic acid (356788-94-8)

Guidance literature:

ethyl 2-diethoxyphosphorylpropionate; With n-butyllithium; In tetrahydrofuran; hexane; at 20 ℃; for 0.333333h;

N-(t-butoxycarbonyl)glycinal; In tetrahydrofuran; hexane; at -78 ℃; for 3h;

With sodium hydroxide; In ethanol; water; at 20 ℃;

DOI:10.1021/jo051483y

Reference yield:

(trans)-4-[(t-butoxycarbonyl)amino]-2-methyl-2-butenoic acid (128121-02-8) → (E) 4-amino-2-methylbut-2-en-1-ol-hydrochloride (128121-04-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.)EtOCOCl/Et₃N 2.)NaBH₄ / 1.) dry THF 2.) H₂O, 4h

2: 85 percent / 10percent aq. HCl / 1 h / Ambient temperature

With hydrogenchloride; sodium tetrahydroborate; chloroformic acid ethyl ester; triethylamine;

DOI:10.1016/0031-9422(90)80004-Z

upstream raw materials:

2-(diethylphosphono)propionic acid

N-(t-butoxycarbonyl)glycinal

ethyl 2-diethoxyphosphorylpropionate

Downstream raw materials:

(E) 4-amino-2-methylbut-2-en-1-ol-hydrochloride