4530-18-1

Basic information

• Product Name: BOC-DL-PHE-OH
• Synonyms: BOC-DL-PHENYLALANINE;BOC-DL-PHE-OH;N-ALPHA-T-BUTOXYCARBONYL-D-PHENYLALANINE;N-tert-Butoxycarbonyl-DL-phenylalanine;N-Methyl-Boc-D-phenylalanine;Boc-N-Me-Phe-OH;BOC-DL-Phenylalanine(Boc-DL-Phe-OH);2-(tert-butoxycarbonyl(Methyl)aMino)-3-phenylpropanoic acid
• CAS NO: 4530-18-1
• Molecular Formula: C₁₄H₁₉NO₄
• Molecular Weight: 279.33
• EINECS: 1533716-785-6
• Product Categories: Phenylalanine [Phe, F]
• Mol File: 4530-18-1.mol

Chemical Properties

• Melting Point: 106-108 °C
• Boiling Point: 405oC at 760 mmHg
• Flash Point: 198.8oC
• Appearance: /Solid
• Density: 1.146g/cm3
• Vapor Pressure: 2.75E-07mmHg at 25°C
• Refractive Index: 1.529
• Storage Temp.: Store at RT.
• PKA: 3.88±0.10(Predicted)
• CAS DataBase Reference: BOC-DL-PHE-OH(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-DL-PHE-OH(4530-18-1)
• EPA Substance Registry System: BOC-DL-PHE-OH(4530-18-1)

Safety Data

• Hazard Codes: Xi
• Statements: 43
• Safety Statements: 36/37
• Hazardous Substances Data: 4530-18-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical and Medicinal Research:
BOC-DL-PHE-OH is utilized as a protective group in peptide synthesis for its ability to safeguard the amino group of phenylalanine, facilitating the formation of desired peptide chains without unwanted side reactions. Its easy removal post-assembly makes it a valuable tool in the development of biologically active peptides and proteins.
Used in the Production of Biologically Active Peptides and Proteins:
In the biotechnology and pharmaceutical industries, BOC-DL-PHE-OH serves as a key component in the synthesis of peptides and proteins with specific biological activities. Its protective function ensures the accurate and efficient production of these molecules, which are vital for various therapeutic applications.

InChI:InChI=1/C15H21NO4/c1-15(2,3)20-14(19)16(4)12(13(17)18)10-11-8-6-5-7-9-11/h5-9,12H,10H2,1-4H3,(H,17,18)

Upstream product

• 150-30-1 Phenylalanine 
• 13303-10-1 tert-Butyl 4-nitrophenyl carbonate 
• 89037-64-9 1-tert-butoxycarbonyloxybenzotriazole 
• 4316-58-9 tris(p-bromophenyl)amine radical cation 
• 126686-59-7 (±)-(4-methoxyphenyl)methyl-2-[(tert-butoxycarbonyl)amino]phenylpropionate 
• 4530-20-5 BOC-glycine 
• 100-39-0 benzyl bromide 
• 24424-99-5 di-tert-butyl dicarbonate 
• 909114-65-4 tert-butyl 4,6-dimethoxy-1,3,5-triazinyl carbonate 
• 75-65-0 tert-butyl alcohol 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 5680-79-5 glycine ethyl ester hydrochloride 
• 35909-82-1 2,3,4,6-tetra-O-benzyl-1-O-(N-tert-butoxycarbonyl-L-phenylalanyl)-β-D-glucopyranose 
• 74293-09-7 2-tert-Butoxycarbonylamino-3-phenyl-propionic acid (2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl ester 

Downstream Products

• 100153-35-3 N-(N-tert-butoxycarbonyl-phenylalanyl)-β-alanine ethyl ester 
• 106572-02-5 N-(N-tert-butoxycarbonyl-DL-phenylalanyl)-glycine methyl ester 
• 721-66-4 glycylphenylalanine 
• 53261-97-5 2-tert-Butoxycarbonylamino-3-phenyl-propionic acid vinyl ester 
• 24281-92-3 (6R)-3-acetoxymethyl-7t-[(N-tert-butoxycarbonyl-Ξ-phenylalanyl)-amino]-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 
• 94732-07-7 Boc-N-ethyl-D,L-phenylalanine 
• 145280-02-0 (1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyl (R)-2-<(tert-butoxycarbonyl)amino>-3-phenylpropanoate 
• 145280-02-0 (1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyl (S)-2-<(tert-butoxycarbonyl)amino>-3-phenylpropanoate 
• 64-04-0 phenethylamine 
• 132385-20-7 (1-{[1-(6,7-Dimethoxy-quinazolin-4-yl)-piperidin-4-ylmethyl]-carbamoyl}-2-phenyl-ethyl)-carbamic acid tert-butyl ester 
• 125719-13-3 Boc-Phe-Gly-OEt 
• 183206-27-1 2-[2-(2-tert-Butoxycarbonylamino-3-phenyl-propionylamino)-benzoylamino]-benzoic acid methyl ester 
• 53331-94-5 Boc-Phe-SePh 
• 202979-80-4 (2'RS)-N-(tert-butoxycarbonyl)phenylalanyl-N⁴,N⁸-bis(tert-butoxycarbonyl)spermidine 

Relevant articles and documents

A Facile Approach to the Synthesis of Benzothiazoles from N-Protected Amino Acids

Abstract: –A simple trituration method for the synthesis of 2-substituted benzothiazoles derived from N-protected amino acids and 2-aminothiophenol using molecular iodine as a mild Lewis acid catalyst has been proposed. The reaction occurs in one step for 20–25 min in solve-free conditions and provides the target products in excellent yields.

Synthesis and anti-tumor activity evaluation of novel 7-fluoro-4-(1-piperazinyl) quinolines

Background: Three series of new 7-fluoro-4-(1-piperazinyl) quinolines (I1~I6, II1~II2 and IV1~IV4) were synthesized. Their anti-tumor activity was evaluated in vitro against three human carcinoma cell lines, namely SGC-7901 cells, BEL-7402 cells and A549 cells expressing high levels of EGFR by Methyl Thiazolyl Terazolium (MTT) assay. Methods: Three series of quinoline derivatives were synthesized, characterized and evaluated for their in vitro anti-tumor activities. Results and Discussion: Structures of the newly synthesized compounds were confirmed by spectral analysis. The preliminary bioassay indicated that compounds I1, I10 and II1 exhibited better anti-tumor activity than the rest of the target compounds and gefitinib against A549 cell based assay, which demonstrated that compounds I1, I10 and II1 are potential agents for cancer therapy. Results suggested that the substitutes on piperazinyl influenced anti-tumor activities remarkably. Conclusion: These results are useful for discovering more potent novel anti-tumor compounds and further studies are ongoing.

Tertiary-butoxycarbonyl (Boc) – A strategic group for N-protection/deprotection in the synthesis of various natural/unnatural N-unprotected aminoacid cyanomethyl esters

A number of cyanomethyl esters of natural/unnatural aminoacids with un-protected amino functionality were synthesized because of their synthetic and medicinal importance. Critical N-Boc deprotection methods in the presence of labile (hydrolytic sensitivity) cyanomethyl functionality were screened thoroughly and it was found that readily available 4M HCl in 1,4-dioxane solution (2–4 equiv); acetonitrile, 0 °C, 2–4 h was a suitable condition. This condition was generalized and successfully applied to a variety of alkyl, alkynyl, aryl, heteroaryl, benzyl, azido, spiro amino acid cyanomethylesters irrespective of the nature of the amine (primary or secondary) and the distance between the amine and ester group to achieve final deprotected amino esters with high yield, and purity compared to other commonly known N-protecting groups (Cbz, Fmoc, Ac, Bn, Bz etc.). It was also demonstrated that N-Boc protected aminoacid cyanomethylesters are stable enough to carry out further functionalization compared to N-unprotected counterparts.

Amino acid conjugated antimicrobial drugs: Synthesis, lipophilicity- activity relationship, antibacterial and urease inhibition activity

Present work describes the in vitro antibacterial evaluation of some new amino acid conjugated antimicrobial drugs. Structural modification was attempted on the three existing antimicrobial pharmaceuticals namely trimethoprim, metronidazole, isoniazid. Twenty one compounds from seven series of conjugates of these drugs were synthesized by coupling with some selected Boc-protected amino acids. The effect of structural features and lipophilicity on the antibacterial activity was investigated. The synthesized compounds were evaluated against five standard American type culture collection (ATCC) i.e. Staphylococcus aureus, Bacillus subtilis, Escherichia coli, Pseudomonas aeruginosa and Salmonella typhi strains of bacteria. Our results identified a close relationship between the lipophilicity and the activity. Triazine skeleton proved beneficial for the increase in hydrophobicity and potency. Compounds with greater hydrophobicity have shown excellent activities against Gram-negative strains of bacteria than Gram-positive. 4-amino unsubstituted trimethoprim-triazine derivative 7b have shown superior activity with MIC = 3.4 μM (2 μg/mL) for S. aureus and 1.1 μM (0.66 μg/mL) for E. coli. The synthesized compounds were also evaluated for their urease inhibition study. Microbial urease from Bacillus pasteurii was chosen for this study. Triazine derivative 7a showed excellent inhibition with IC50 = 6.23 ± 0.09 μM. Docking studies on the crystal structure of B. pasteurii urease (PDB ID 4UBP) were carried out.

Visible Light Photorelease of Carboxylic Acids via Charge-Transfer Excitation of N-Methylpyridinium Iodide Esters

Iodide contrast sensitization to direct irradiation of charge transfer salts incurs carboxylic acid release via visible light absorption. The photochemical reduction of N-methyl-4-pyridinium iodide esters to release carboxylic acids is examined using 1H NMR analysis. Photolysis reactions are carried out under mild, biphasic solvent conditions using a household LED lamp. Carboxylic acid release is reported in high yields, and the viability of this method for synthetic chemistry is demonstrated through a macroscale reaction.

Iron-catalyzed oxidative C - H/C - H cross-coupling: An efficient route to α-quaternary α-amino acid derivatives

Fully loaded: A coordinating activation strategy has been developed to furnish α-quaternary α-amino acids through the iron(III)-catalyzed oxidative functionalization of α-C(sp3) - H bonds of α-tertiary α-amino acid esters. The reaction exhibits a broad substrate scope for both α-amino acids and nucleophiles (Nu) as well as good functional-group tolerance (see scheme, DTBP=di-tert-butyl peroxide, DCE=1,2-dichloroethane). Copyright

Enantiomeric resolution of α-amino acid derivatives on two diastereomeric chiral stationary phases based on chiral crown ethers incorporating two different chiral units

Two diastereomeric chiral stationary phases (CSPs) were applied to the liquid chromatographic resolution of various racemic a-amino methyl esters, α-amino N,N-diethylamides and α-amino N-propylamides. The CSP incorporating (R)-3,3' -diphenyl-1,1' -binaphtyl and (R,R)-tartaric acid unit as chiral barriers did not show any chiral recognition. In contrast, the CSP incorporating (R)-3,3'-diphenyl-1,1'-binaphtyl and (S,S)-tartaric acid unit as chiral barriers was found to show excellent chiral recognition especially for the two enantiomers of a-amino N-propylamides. Some of a-amino methyl esters and α-amino N,N-diethylamides were also resolved on the CSP incorporating (R)-3,3'-diphenyl-1,1'-binaphtyl and (S,S)-tartaric acid unit. From these results it was concluded that the two chiral units composing the diastereomeric CSPs can show "matched" or "mismatched" effect on the chiral recognition according to their absolute stereochemistry.

Kinetic resolution of racemic carboxylic acids by an L-histidine-derived sulfonamide-induced enantioselective esterification reaction

(Chemical Equation Presented) The direct and catalytic kinetic resolution of racemic carboxylic acids bearing a Bronsted base such as O-protected α-hydroxy carboxylic acids and N-protected α-amino acids has been accomplished through an L-histidine-derived sulfonamide-induced enantioselective esterification reaction with tert-butyl alcohol for the first time. Highly asymmetric induction [S(kfast/kslow) = up to 56] has been achieved under the equilibrium between a chiral catalyst and two diastereomeric acylammonium salts through an intramolecular hydrogen-bonding interaction.

Useful reagents for introduction of Boc and Fmoc protective groups to amines: Boc-DMT and Fmoc-DMT

New amino-protecting reagents, Boc-DMT and Fmoc-DMT, were prepared, and found to be useful for the introduction of Boc and Fmoc groups into amines. Both the reagents can protect various amines including amino acids in good yield in aqueous media. Since the reagents are neither unstable nor irritating, they are practically useful. Georg Thieme Verlag Stuttgart.

Enzymatic removal of carboxyl protecting groups. 1. Cleavage of the tert-butyl moiety

(Chemical Equation Presented) A recent discovery that a certain amino acid motif (GGG-(A)X-motif) in lipases and esterases determines their activity toward tertiary alcohols prompted us to investigate the use of these biocatalysts in the mild and selective removal of tert-butyl protecting groups in amino acid derivatives and related compounds. An esterase from Bacillus subtilis (BsubpNBE) and lipase A from Candida antarctica (CAL-A) were identified as the most active enzymes, which hydrolyzed a range of tert-butyl esters of protected amino acids (e.g., Boc-Tyr-OtBu, Z-GABA-OtBu, Fmoc-GABA-O tBu) in good to high yields and left Boc, Z, and Fmoc-protecting groups intact.