2-Acetamido-4-methylpent-4-enoic acid

Base Information

• Chemical Name: 2-Acetamido-4-methylpent-4-enoic acid
• CAS No.: 87325-65-3
• Molecular Formula: C₈H₁₃NO₃
• Molecular Weight: 171.196
• Hs Code.: 2924199090
• DSSTox Substance ID: DTXSID30557496
• Mol file: 87325-65-3.mol

Synonyms:87325-65-3;2-ACETAMIDO-4-METHYLPENT-4-ENOIC ACID;N-ACETYL-4,5-DEHYDRO-DL-LEUCINE;N-acetyl-4-methylidenenorvaline;DTXSID30557496;AKOS005604823;AS-40815;CS-0267038;2-ACETAMIDO-4-METHYLPENT-4-ENOICACID;EN300-297909;A842085;METHYL5-[(PHENYLSULFONYL)METHYL]-2-FUROATE;F2147-6639;Z1198151249

Chemical Property of 2-Acetamido-4-methylpent-4-enoic acid

Chemical Property:

• PSA: 66.40000
• LogP: 0.93280
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 171.08954328
• Heavy Atom Count: 12
• Complexity: 210

Purity/Quality:

98%min ^*data from raw suppliers

N-Acetyl-4,5-dehydro-DL-leucine ^*data from reagent suppliers

Safty Information:

• Safety Statements: S22:Do not inhale dust.; S24/25:Avoid contact with skin and eyes.

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=C)CC(C(=O)O)NC(=O)C
• Uses: N-Acetyl-4,5-dehydro-DL-leucine is an intermediate in the synthesis of DL-[4,5-T]leucine.

Technology Process of 2-Acetamido-4-methylpent-4-enoic acid

There total 5 articles about 2-Acetamido-4-methylpent-4-enoic 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: 89.0%

N-acetylglycine-(2-methallyl) ester → (R,S)-2-acetamido-4-methyl-4-pentenoic acid (87325-65-3,88547-24-4)

Guidance literature:

With zinc(II) chloride; lithium diisopropyl amide; In tetrahydrofuran; at -78 - 20 ℃; Schlenk technique;

DOI:10.1039/c6ob00800c

Reference yield:

2-acetamido-2-(2-methylallyl)malonic acid (855650-97-4) → (R,S)-2-acetamido-4-methyl-4-pentenoic acid (87325-65-3,88547-24-4)

Guidance literature:

at 160 ℃;

DOI:10.1021/ja01615a058

Reference yield:

ethyl 2-acetamido-2-ethoxycarbonyl-4-methyl-4-pentenoic acid (37944-29-9) → (R,S)-2-acetamido-4-methyl-4-pentenoic acid (87325-65-3,88547-24-4)

Guidance literature:

With sodium carbonate;

DOI:10.1021/ja01159a502

upstream raw materials:

2-acetamido-2-(2-methylallyl)malonic acid

ethyl 2-acetamido-2-ethoxycarbonyl-4-methyl-4-pentenoic acid

2-acetylaminomalonic acid diethyl ester

3-Chloro-2-methylpropene

Downstream raw materials:

(R)-2-acetamido-4-methyl-4-pentenoic acid

(2S)-2-tert-butoxycarbonylamino-4-methyl-4-pentenoic acid

N-fluoren-9-ylmethyloxycarbonyl-4,5-dehydro-L-leucine

(2S)-2-amino-4-methylpent-4-enoic acid

Refernces

• 1、 Barbie, Philipp,Kazmaier, Uli. "Total synthesis of cyclomarins A, C and D, marine cyclic peptides with interesting anti-tuberculosis and anti-malaria activities". . p. 6036 - 6054. Retrieved 2016/07/06.
• 2、 Schmidt,Schmidt. "The total synthesis of eponemycin". . p. 300 - 304. Retrieved 2007/10/02.