(R)-4-Bromo-2-((tert-butoxycarbonyl)amino)pent-4-enoic acid

Base Information

• Chemical Name: (R)-4-Bromo-2-((tert-butoxycarbonyl)amino)pent-4-enoic acid
• CAS No.: 149930-92-7
• Molecular Formula: C₁₀H₁₆BrNO₄
• Molecular Weight: 294.145
• Hs Code.: 2924199090
• DSSTox Substance ID: DTXSID80426542
• Wikidata: Q82239434
• Mol file: 149930-92-7.mol

Synonyms:149930-92-7;Boc-D-2-Amino-4-bromo-4-pentenoic acid;(R)-4-Bromo-2-((tert-butoxycarbonyl)amino)pent-4-enoic acid;(2R)-4-bromo-2-[(2-methylpropan-2-yl)oxycarbonylamino]pent-4-enoic Acid;DTXSID80426542;MFCD01320883;AKOS016843806;4-Pentenoic acid, 4-bromo-2-[[(1,1-dimethylethoxy)carbonyl]amino]-, (R)- (9CI);PS-12808;A884219;(2R)-4-bromo-2-{[(tert-butoxy)carbonyl]amino}pent-4-enoic acid;4-pentenoic acid, 4-bromo-2-[[(1,1-dimethylethoxy)carbonyl]amino]-, (R)-

Chemical Property of (R)-4-Bromo-2-((tert-butoxycarbonyl)amino)pent-4-enoic acid

Chemical Property:

• Boiling Point: 396.7 °C at 760 mmHg
• PKA: 3.81±0.10(Predicted)
• Flash Point: 193.7 °C
• PSA: 75.63000
• Density: 1.407 g/cm³
• LogP: 2.65390
• Storage Temp.: 2-8°C
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 293.02627
• Heavy Atom Count: 16
• Complexity: 296

Purity/Quality:

99% ^*data from raw suppliers

Boc-D-2-amino-4-bromo-4-pentenoic acid ^*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)Br)C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@H](CC(=C)Br)C(=O)O

Technology Process of (R)-4-Bromo-2-((tert-butoxycarbonyl)amino)pent-4-enoic acid

There total 7 articles about (R)-4-Bromo-2-((tert-butoxycarbonyl)amino)pent-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: 47.6%

tert-butyl chloroformate (24608-52-4) + (S)-2-Amino-4-bromo-pent-4-enoic acid (151144-96-6,264903-49-3) → N-tert-butoxycarbonyl-L-2-amino-4-bromo-4-pentenoic acid (151215-34-8,149930-92-7)

Guidance literature:

With sodium carbonate; In 1,4-dioxane; water; at 30 ℃; for 4h; pH=8 - 9;

Reference yield: 44.8%

N-(tert-butyloxycarbonyl) azide (1070-19-5) + (S)-2-Amino-4-bromo-pent-4-enoic acid (151144-96-6,264903-49-3) → N-tert-butoxycarbonyl-L-2-amino-4-bromo-4-pentenoic acid (151215-34-8,149930-92-7)

Guidance literature:

With sodium carbonate; In tetrahydrofuran; water; at 20 ℃; for 4h; pH=8 - 9;

Reference yield: 43.5%

di-tert-butyl dicarbonate (24424-99-5) + (S)-2-Amino-4-bromo-pent-4-enoic acid (151144-96-6,264903-49-3) → N-tert-butoxycarbonyl-L-2-amino-4-bromo-4-pentenoic acid (151215-34-8,149930-92-7)

Guidance literature:

With sodium carbonate; In water; acetone; at 20 ℃; for 5h; pH=8 - 9; Temperature;

upstream raw materials:

di-tert-butyl dicarbonate

(S)-2-Amino-4-bromo-pent-4-enoic acid

diethyl 2-(2-bromoprop-2-en-1-yl)-2-acetamidopropanedioate

(S)-2-Acetylamino-4-bromo-pent-4-enoic acid

Refernces

• 1、 Lopez, Anna,Pleixats, Roser. "Highly diastereoselective monoalkylation and Michael addition of N- (diphenylmethylene)glycinesultam under solid-liquid phase-transfer catalysis conditions using potassium carbonate as base". . p. 1967 - 1977. Retrieved 2007/10/03.