Production Method 1

1991-87-3

24424-99-5

80102-26-7

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: Water ;  rt
1.2 Solvents: Tetrahydrofuran ,  Water ;  cooled; 2 h, pH 7.5 - 8.5, 0 °C; 24 h, pH 7.5 - 8.5, rt
1.3 Reagents: Hydrochloric acid Solvents: Water ;  pH 2

Reference

A study of the N-tert-butoxycarbonylation of non-natural amino acids

Liu, Yi; et al, Yaoxue Jinzhan, 2006, 30(7), 330-332

Production Method 2

1991-87-3

24424-99-5

80102-26-7

Reaction Conditions

1.1 15 h, 0 °C

Reference

Synthesis and resolution of N-BOC-2-methyl-L-phenylalanine, N-BOC-3-methyl-L-phenylalanine and N-BOC-4-methyl-L-phenylalanine isomers

Li, Xiao-Hui; et al, Gaodeng Xuexiao Huaxue Xuebao, 2008, 29(7), 1363-1366

Production Method 3

80102-26-7

Reaction Conditions

1.1 Reagents: Ammonium hydroxide Solvents: Dimethylformamide ,  Water ;  pH 8, 37 °C
1.2 Catalysts: Subtilisin ;  8 h, pH 8, 37 °C

Reference

Synthesis and resolution of N-BOC-2-methyl-L-phenylalanine, N-BOC-3-methyl-L-phenylalanine and N-BOC-4-methyl-L-phenylalanine isomers

Li, Xiao-Hui; et al, Gaodeng Xuexiao Huaxue Xuebao, 2008, 29(7), 1363-1366

Production Method 4

80102-26-7

Reaction Conditions

1.1 Solvents: Toluene ;  5 h, 110 °C
2.1 Reagents: Sodium hydroxide Solvents: Ethanol ,  Water ;  5 h, 0 °C
2.2 Reagents: Sodium bicarbonate Solvents: Water
3.1 Reagents: Ammonium hydroxide Solvents: Dimethylformamide ,  Water ;  pH 7, 38 °C
3.2 Catalysts: Amidase ;  24 h, pH 7, 38 °C
4.1 15 h, 0 °C

Reference

Synthesis and resolution of N-BOC-2-methyl-L-phenylalanine, N-BOC-3-methyl-L-phenylalanine and N-BOC-4-methyl-L-phenylalanine isomers

Li, Xiao-Hui; et al, Gaodeng Xuexiao Huaxue Xuebao, 2008, 29(7), 1363-1366

Production Method 5

104-81-4

1068-90-2

80102-26-7

Reaction Conditions

1.1 Reagents: Sodium Solvents: Ethanol ;  30 h, 110 °C
1.2 5 h, 110 °C
2.1 Reagents: Sodium hydroxide Solvents: Ethanol ,  Water ;  5 h, 0 °C
2.2 Reagents: Sodium bicarbonate Solvents: Water
3.1 Solvents: Toluene ;  5 h, 110 °C
4.1 Reagents: Sodium hydroxide Solvents: Ethanol ,  Water ;  5 h, 0 °C
4.2 Reagents: Sodium bicarbonate Solvents: Water
5.1 Reagents: Ammonium hydroxide Solvents: Dimethylformamide ,  Water ;  pH 7, 38 °C
5.2 Catalysts: Amidase ;  24 h, pH 7, 38 °C
6.1 15 h, 0 °C

Reference

Synthesis and resolution of N-BOC-2-methyl-L-phenylalanine, N-BOC-3-methyl-L-phenylalanine and N-BOC-4-methyl-L-phenylalanine isomers

Li, Xiao-Hui; et al, Gaodeng Xuexiao Huaxue Xuebao, 2008, 29(7), 1363-1366

Production Method 6

80102-26-7

Reaction Conditions

1.1 Solvents: Toluene ;  5 h, 110 °C
2.1 Reagents: Ammonium hydroxide Solvents: Dimethylformamide ,  Water ;  pH 8, 37 °C
2.2 Catalysts: Subtilisin ;  8 h, pH 8, 37 °C

Reference

Synthesis and resolution of N-BOC-2-methyl-L-phenylalanine, N-BOC-3-methyl-L-phenylalanine and N-BOC-4-methyl-L-phenylalanine isomers

Li, Xiao-Hui; et al, Gaodeng Xuexiao Huaxue Xuebao, 2008, 29(7), 1363-1366

Production Method 7

6955-13-1

80102-26-7

Reaction Conditions

1.1 Reagents: Ammonium hydroxide Solvents: Dimethylformamide ,  Water ;  pH 7, 38 °C
1.2 Catalysts: Amidase ;  24 h, pH 7, 38 °C
2.1 15 h, 0 °C

Reference

Synthesis and resolution of N-BOC-2-methyl-L-phenylalanine, N-BOC-3-methyl-L-phenylalanine and N-BOC-4-methyl-L-phenylalanine isomers

Li, Xiao-Hui; et al, Gaodeng Xuexiao Huaxue Xuebao, 2008, 29(7), 1363-1366

Production Method 8

1119519-52-6

80102-26-7

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: Ethanol ,  Water ;  5 h, 0 °C
1.2 Reagents: Sodium bicarbonate Solvents: Water
2.1 Reagents: Ammonium hydroxide Solvents: Dimethylformamide ,  Water ;  pH 7, 38 °C
2.2 Catalysts: Amidase ;  24 h, pH 7, 38 °C
3.1 15 h, 0 °C

Reference

Synthesis and resolution of N-BOC-2-methyl-L-phenylalanine, N-BOC-3-methyl-L-phenylalanine and N-BOC-4-methyl-L-phenylalanine isomers

Li, Xiao-Hui; et al, Gaodeng Xuexiao Huaxue Xuebao, 2008, 29(7), 1363-1366

Production Method 9

80102-26-7

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: Ethanol ,  Water ;  5 h, 0 °C
1.2 Reagents: Sodium bicarbonate Solvents: Water
2.1 Solvents: Toluene ;  5 h, 110 °C
3.1 Reagents: Ammonium hydroxide Solvents: Dimethylformamide ,  Water ;  pH 8, 37 °C
3.2 Catalysts: Subtilisin ;  8 h, pH 8, 37 °C

Reference

Synthesis and resolution of N-BOC-2-methyl-L-phenylalanine, N-BOC-3-methyl-L-phenylalanine and N-BOC-4-methyl-L-phenylalanine isomers

Li, Xiao-Hui; et al, Gaodeng Xuexiao Huaxue Xuebao, 2008, 29(7), 1363-1366

Production Method 10

104-81-4

102831-44-7

80102-26-7

Reaction Conditions

1.1 Reagents: Sodium Solvents: Ethanol ;  30 h, 110 °C
1.2 5 h, 110 °C
2.1 Reagents: Sodium hydroxide Solvents: Ethanol ,  Water ;  5 h, 0 °C
2.2 Reagents: Sodium bicarbonate Solvents: Water
3.1 Solvents: Toluene ;  5 h, 110 °C
4.1 Reagents: Ammonium hydroxide Solvents: Dimethylformamide ,  Water ;  pH 8, 37 °C
4.2 Catalysts: Subtilisin ;  8 h, pH 8, 37 °C

Reference

Synthesis and resolution of N-BOC-2-methyl-L-phenylalanine, N-BOC-3-methyl-L-phenylalanine and N-BOC-4-methyl-L-phenylalanine isomers

Li, Xiao-Hui; et al, Gaodeng Xuexiao Huaxue Xuebao, 2008, 29(7), 1363-1366

Production Method 11

82291-79-0

80102-26-7

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: Ethanol ,  Water ;  5 h, 0 °C
1.2 Reagents: Sodium bicarbonate Solvents: Water
2.1 Solvents: Toluene ;  5 h, 110 °C
3.1 Reagents: Sodium hydroxide Solvents: Ethanol ,  Water ;  5 h, 0 °C
3.2 Reagents: Sodium bicarbonate Solvents: Water
4.1 Reagents: Ammonium hydroxide Solvents: Dimethylformamide ,  Water ;  pH 7, 38 °C
4.2 Catalysts: Amidase ;  24 h, pH 7, 38 °C
5.1 15 h, 0 °C

Reference

Synthesis and resolution of N-BOC-2-methyl-L-phenylalanine, N-BOC-3-methyl-L-phenylalanine and N-BOC-4-methyl-L-phenylalanine isomers

Li, Xiao-Hui; et al, Gaodeng Xuexiao Huaxue Xuebao, 2008, 29(7), 1363-1366

Boc-4-Methylphenylalanine Raw materials

• 4-Methyl-L-phenylalanine
• 4-Methylbenzyl bromide
• Di-tert-butyl dicarbonate
• 1,3-diethyl 2-acetamidopropanedioate
• 2-acetamido-3-(4-methylphenyl)propanoic Acid
• diethyl (acetylamino)(4-methylbenzyl)propanedioate
• Diethyl (Boc-amino)malonate
• N-Acetyl-DL-(4-methylphenyl)alanine ethyl ester

Boc-4-Methylphenylalanine Preparation Products

• Boc-4-Methylphenylalanine (80102-26-7)

• 1. Fatty acid eutectic mixtures and derivatives from non-edible animal fat as phase change materials?
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• 4. Excitation energies from ground-state density-functionals by means of generator coordinates
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• 5. Evolutionary de novo design of phenothiazine derivatives for dye-sensitized solar cells?
  Vishwesh Venkatraman,Marco Foscato,Vidar R. Jensen,Bj?rn K?re Alsberg J. Mater. Chem. A, 2015,3, 9851-9860

• Solvents and Organic Chemicals Organic Compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Amino acids and derivatives
• Solvents and Organic Chemicals Organic Compounds Acids/Esters

Professional Introduction to Boc-4-Methylphenylalanine (CAS No. 80102-26-7)

Boc-4-Methylphenylalanine, with the chemical name N-Boc-4-methylphenylalanine, is a crucial intermediate in the field of pharmaceutical synthesis. This compound, identified by its CAS number 80102-26-7, plays a significant role in the development of various therapeutic agents. Its molecular structure, characterized by a benzyloxy carbonyl (Boc) protecting group on the amino nitrogen and a 4-methylphenylalanine side chain, makes it a valuable building block for peptide and protein drug synthesis.

The Boc group in Boc-4-Methylphenylalanine serves as an amino acid protecting group, which is essential in multi-step organic synthesis. It prevents unwanted side reactions by masking the reactive amine group during subsequent chemical transformations. This protective feature is particularly useful in peptide coupling reactions, where maintaining the integrity of each amino acid's functional groups is critical for achieving high yields and purity.

Recent advancements in pharmaceutical chemistry have highlighted the importance of protected amino acids like Boc-4-Methylphenylalanine in drug development. The compound's versatility has been leveraged in the synthesis of bioactive peptides and peptidomimetics. For instance, researchers have utilized Boc-4-Methylphenylalanine to create novel inhibitors targeting specific enzymatic pathways involved in diseases such as cancer and inflammation.

In the realm of medicinal chemistry, Boc-4-Methylphenylalanine has been instrumental in the design of peptidomimetics that mimic the structure and function of natural peptides while exhibiting improved pharmacokinetic properties. These peptidomimetics are being explored for their potential in treating neurological disorders, cardiovascular diseases, and infectious diseases. The 4-methylphenylalanine side chain contributes to the stability and bioavailability of these synthetic peptides, enhancing their therapeutic efficacy.

The use of Boc-4-Methylphenylalanine in solid-phase peptide synthesis (SPPS) has also gained significant attention. SPPS is a widely employed technique for constructing complex peptides efficiently. The incorporation of Boc-protected amino acids into peptide chains allows for controlled deprotection steps, ensuring precise sequence assembly. This method has been particularly valuable in producing therapeutic proteins such as antibodies and growth factors.

Furthermore, the incorporation of 4-methylphenylalanine into peptide structures has been associated with improved binding affinity to target receptors. This modification can enhance the pharmacological activity of peptides by optimizing their interactions with biological targets. For example, studies have demonstrated that peptides containing 4-methylphenylalanine analogs exhibit stronger binding to certain proteases involved in cancer progression, making them promising candidates for antitumor therapies.

Recent research has also explored the role of Boc-protected amino acids in drug delivery systems. The Boc group can be selectively removed under specific conditions, allowing for controlled release of active pharmaceutical ingredients (APIs). This property has been exploited in designing smart drug delivery platforms that respond to physiological stimuli, thereby improving treatment outcomes.

The industrial production of Boc-4-Methylphenylalanine adheres to stringent quality control measures to ensure consistency and purity. Manufacturers employ advanced synthetic methodologies and purification techniques to meet the demands of pharmaceutical applications. The compound's high-quality standards are essential for ensuring the safety and efficacy of final drug products.

In conclusion, Boc-4-Methylphenylalanine (CAS No. 80102-26-7) is a vital intermediate in pharmaceutical synthesis with broad applications in drug development. Its protective group functionality and structural versatility make it indispensable in peptide and protein drug synthesis. Recent advancements in medicinal chemistry continue to highlight its significance, paving the way for innovative therapeutic strategies across various disease domains.

• 57292-45-2((2R)-2-(tert-butoxycarbonylamino)-3-(4-fluorophenyl)propanoic acid)
• 41153-30-4((S)-2-((tert-Butoxycarbonyl)amino)-3-(4-fluorophenyl)propanoic acid)
• 37553-65-4(Boc-N-Me-Phe-OH)
• 13734-34-4((2S)-2-(tert-butoxycarbonylamino)-3-phenyl-propanoic acid)
• 53267-93-9(Boc-Tyr(Me)-OH)
• 76985-10-9((R)-2-((tert-Butoxycarbonyl)amino)-3-(naphthalen-2-yl)propanoic acid)
• 55533-24-9((S)-3-(4-Aminophenyl)-2-((tert-butoxycarbonyl)amino)propanoic acid)
• 18942-49-9(Boc-D-Phe-OH)
• 51987-73-6(N-Boc-L-phenylalanine methyl ester)
• 3978-80-1(N-Boc-L-tyrosine)