2900-27-8

Basic information

• Product Name: BOC-D-PHG-OH
• Synonyms: (2S)-[(tert-butoxycarbonyl)aMino](phenyl)ethanoic acid;(S)-2-((tert-Butoxycarbonyl)aMino)-2-phenylacetic acid;N-(tert-Butoxycarbonyl)-L-2-phenylglycine, 98.0%(LC);(S)-Boc-2-aminophenylacetic acid;Boc-L-phenylglycine99%;N-Boc-L-2-phenylglycine,99%e.e.;BOC-D-ALPHA-PHENYLGLYCINE;BOC-D-A-PHENYLGLYCINE
• CAS NO: 2900-27-8
• Molecular Formula: C₁₃H₁₇NO₄
• Molecular Weight: 251.28
• EINECS: -0
• Product Categories: Amino Acid Derivatives;Amino Acids;Phenylglycine [Phg];Unusual Amino Acids;Amino Acids (N-Protected);Biochemistry;Boc-Amino Acids;Boc-Amino acid series
• Mol File: 2900-27-8.mol

Chemical Properties

• Melting Point: 88-91 °C
• Boiling Point: 407.2 °C at 760 mmHg
• Flash Point: 200.1 °C
• Appearance: /
• Density: 1.182 g/cm³
• Vapor Pressure: 2.32E-07mmHg at 25°C
• Refractive Index: 142 ° (C=1, EtOH)
• Storage Temp.: Store at RT.
• PKA: 3.51±0.10(Predicted)
• Water Solubility: Insoluble in water
• BRN: 3592362
• CAS DataBase Reference: BOC-D-PHG-OH(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-D-PHG-OH(2900-27-8)
• EPA Substance Registry System: BOC-D-PHG-OH(2900-27-8)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 2900-27-8(Hazardous Substances Data)

Usage

Chemical Properties

White to off-white crystalline powder

InChI:InChI=1/C13H17NO4/c1-13(2,3)18-12(17)14-10(11(15)16)9-7-5-4-6-8-9/h4-8,10H,1-3H3,(H,14,17)(H,15,16)/t10-/m0/s1

Upstream product

• 13303-10-1 tert-Butyl 4-nitrophenyl carbonate 
• 2835-06-5 phenylglycin 
• 124-38-9 carbon dioxide 
• 42116-44-9 N-tert-butoxycarbonylbenzylamine 
• 102089-74-7 tert-butyl 2-hydroxy-1-phenylethylcarbamate 
• 1070-19-5 N-(tert-butyloxycarbonyl) azide 
• 219580-24-2 3,5-Dimethyl-pyrazole-1-carboxylic acid tert-butyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 4530-20-5 BOC-glycine 
• 117049-08-8 (1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyl<(tert-butoxycarbonyl)amino>bromoacetate 
• 15028-39-4 L-2-phenylglycine methyl ester hydrochloride 
• 4248-19-5 tert-butyl carbazate 
• 150884-50-7 benzaldehyde N-boc imine 
• 155396-71-7 tert-butyl N-(phenyl(phenylsulfonyl)methyl)carbamate 

Downstream Products

• 3573-13-5 6β-((Ξ)-2-tert-butoxycarbonylamino-2-phenyl-acetylamino)-penicillanic acid 
• 7716-28-1 (6R)-3-acetoxymethyl-7t-((S)-2-tert-butoxycarbonylamino-2-phenyl-acetylamino)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 
• 62166-97-6 (6R)-7t-((R)-tert-butoxycarbonylamino-phenyl-acetylsulfanyl)-3-methyl-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 2,2,2-trichloro-ethyl ester 
• 62166-87-4 6β-((R)-tert-butoxycarbonylamino-phenyl-acetylsulfanyl)-penicillanic acid 2,2,2-trichloro-ethyl ester 
• 139975-06-7 (6R)-7t-((R)-2-tert-butoxycarbonylamino-2-phenyl-acetylamino)-3-(5-methyl-[1,3,4]thiadiazol-2-ylsulfanylmethyl)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 
• 136329-30-1 (2-Oxo-1-phenyl-2-pyrrolidin-1-yl-ethyl)-carbamic acid tert-butyl ester 
• 143978-88-5 N-tert-butoxycarbonyl-L-phenylglycine methyl ester 
• 122751-58-0 Ac-Ala-Pgl-Ala-Lys-NH₂ 
• 141261-61-2 Cyclo(-Arg(Tos)-Gly-Asp(OcHex)-Phg-)2 
• 141261-60-1 Cyclo(-Arg(Tos)-Gly-Asp(OcHex)-Phg-) 
• 141261-62-3 Cyclo(-Arg-Gly-Asp-Phg-) 
• 201152-47-8 Boc-Phg-OSu 
• 117194-49-7 Boc-Phg-O-iBu 
• 2900-28-9 Z-Thr(Boc-Phg-O-)-OH 

Relevant articles and documents

Crystallization method of Boc-amino acid

The invention belongs to the technical field of medicinal chemistry, and particularly relates to a crystallization method of Boc amino acid. The preparation method comprises the following steps: (1) reacting free amino acid with di-tert-butyl dicarbonate, carrying out post-treatment to obtain a Boc-protected amino acid reaction solution, and carrying out reduced pressure distillation to remove a solvent until the solvent is dry, thereby obtaining a colorless or light yellow transparent oily substance; (2) adding a seed crystal into the obtained oily substance, standing for a period of time at normal temperature, curing the oily substance to be white, and then adding a weak polar solvent for pulping; (3) pulping for a period of time, filtering, washing, and drying under reduced pressure to obtain the product. According to the method, crystallized Boc amino acid cannot be separated out and crystallized by a conventional method, so that the purity of the product is improved, and meanwhile, the product has certain stability and can be stored for a long time without being decomposed.

Synthesis ofN-Boc-α-amino Acids from Carbon Dioxide by Electrochemical Carboxylation ofN-Boc-α-aminosulfones

Electrochemical reduction ofN-Boc-α-aminosulfones in DMF using an undivided cell equipped with a Pt plate cathode and an Mg rod anode under atmospheric pressure of bubbling carbon dioxide through the solution under constant current conditions resulted in a reductive C-S bond cleavage with elimination of benzenesulfinate ion generating the corresponding anion species followed by fixation of carbon dioxide to give the correspondingN-Boc-α-amino acids in moderate to good yields.

Discovery of M3Antagonist-PDE4 Inhibitor Dual Pharmacology Molecules for the Treatment of Chronic Obstructive Pulmonary Disease

In this paper, we report the discovery of dual M3 antagonist-PDE4 inhibitor (MAPI) compounds for the inhaled treatment of pulmonary diseases. The identification of dual compounds was enabled by the intuition that the fusion of a PDE4 scaffold derived from our CHF-6001 series with a muscarinic scaffold through a common linking ring could generate compounds active versus both the transmembrane M3 receptor and the intracellular PDE4 enzyme. Two chemical series characterized by two different muscarinic scaffolds were investigated. SAR optimization was aimed at obtaining M3 nanomolar affinity coupled with nanomolar PDE4 inhibition, which translated into anti-bronchospastic efficacy ex vivo (inhibition of rat trachea contraction) and into anti-inflammatory efficacy in vitro (inhibition of TNFα release). Among the best compounds, compound 92a achieved the goal of demonstrating in vivo efficacy and duration of action in both the bronchoconstriction and inflammation assays in rat after intratracheal administration.

COMPOUNDS USEFUL IN HIV THERAPY

The invention relates to compounds of Formula (I), (Ia), (Ib), (II) or (III), salts thereof, pharmaceutical compositions thereof, as well as therapeutic methods of treatment and prevention.

One-Pot C-H Arylation/Lactamization Cascade Reaction of Free Benzylamines

An efficient method has been developed for the synthesis of seven-membered biaryl lactams involving Pd-catalyzed, native amine-directed, ortho-arylation of benzylamines followed by in situ lactamization. This cascade sequence is enabled by the use of 2-iodobenzoates, which facilitates C-H arylation from the free amine under conditions that typically require an improved directing group approach. This reaction is characterized by a broad substrate scope with good functional group tolerance. The need for an ester versus carboxylic acid-functionalized coupling partner is also explored, as is the potential for synthesizing eight-membered biaryl lactams. Various applications are also investigated, including access to the aza-brassinolide core.

Asymmetric Dearomative Cascade Multiple Functionalizations of Activated N-Alkylpyridinium and N-Alkylquinolinium Salts

An enantioselective cascade reaction of N-alkylpyridinium and -quinolinium salts with o-hydroxybenzylideneacetones to access fused polyheterocycles through cross dienamine-mediated addition followed by trapping of the dearomatized enamine-type intermediates and aminal formation has been developed. A cascade assembly of N-benzyl-4-methylpyridinium salt and cyclic 2,4-dienones is further disclosed to give bridged frameworks via repetitive dearomatization and aromatization activation.

ALLOSTERIC EGFR INHIBITORS AND METHODS OF USE THEREOF

The disclosure relates to compounds that act as an allosteric inhibitors of epidermal growth factor receptor (EGFR); pharmaceutical compositions comprising the compounds; and methods of treating or preventing kinase-mediated disorders, including cancer and other proliferation diseases.

Carbon Dioxide-Mediated C(sp2)-H Arylation of Primary and Secondary Benzylamines

C-C bond formation by transition metal-catalyzed C-H activation has become an important strategy to fabricate new bonds in a rapid fashion. Despite the pharmacological importance of ortho-arylbenzylamines, however, effective ortho-C-C bond formation of free primary and secondary benzylamines using PdII remains an outstanding challenge. Presented herein is a new strategy for constructing ortho-arylated primary and secondary benzylamines mediated by carbon dioxide (CO2). The use of CO2 with Pd is critical to allowing this transformation to proceed under relatively mild conditions, and mechanistic studies indicate that it (CO2) is directly involved in the rate-determining step. Furthermore, the milder temperatures furnish free amine products that can be directly used or elaborated without the need for deprotection. In cases where diarylation is possible, an interesting chelate effect is shown to facilitate selective monoarylation.

Structural modification of histone deacetylase inhibitors with a phenylglycine scaffold

During the discovery of histone deacetylase inhibitors (HDACIs) as antitumor drugs, a series of potent phenylglycine-based HDACIs were developed. However, further development is restricted by the poor solubility. Therefore, structural modifications were performed in the present study in the development of potent HDACIs with improved pharmacokinetic properties. The synthesized molecules were designed by the substitution of fatty linkers for aromatic linkers, and showed good solubility profiles. Among the compounds derived, molecule HD9 showed a potent enzyme-inhibitory effect (IC50 values of 76 nmol/l) and in-vitro antiproliferative activities (IC50 values of 0.51, 0.83, and 0.76 μmol/l against U937, K562, and HL60 cells, respectively). Molecule HD9 showed selectivity of HDAC3 over HDAC6 in the isoform selectivity assays. Molecular docking studies showed good binding patterns of molecule HD9 to the active site of HDAC3. Results from the present work indicated that molecule HD9 is a promising lead compound for the tumor therapy.

Synthesis of Tripeptide Derivatives with Three Stereogenic Centers and Chiral Recognition Probed by Tetraaza Macrocyclic Chiral Solvating Agents Derived from d -Phenylalanine and (1 S,2 S)-(+)-1,2-Diaminocyclohexane via 1H NMR Spectroscopy

Enantiomers of a series of tripeptide derivatives with three stereogenic centers (±)-G1-G9 have been prepared from d- and l-α-amino acids as guests for chiral recognition by 1H NMR spectroscopy. In the meantime, a family of tetraaza macrocyclic chiral solvating agents (TAMCSAs) 1a-1d has been synthesized from d-phenylalanine and (1S,2S)-(+)-1,2-diaminocyclohexane. Discrimination of enantiomers of (±)-G1-G9 was carried out in the presence of TAMCSAs 1a-1d by 1H NMR spectroscopy. The results indicate that enantiomers of (±)-G1-G9 can be effectively discriminated in the presence of TAMCSAs 1a-1d by 1H NMR signals of multiple protons exhibiting nonequivalent chemical shifts (ΔΔδ) up to 0.616 ppm. Furthermore, enantiomers of (±)-G1-G9 were easily assigned by comparing 1H NMR signals of the split corresponding protons with those attributed to a single enantiomer. Different optical purities (ee up to 90%) of G1 were clearly observed and calculated in the presence of TAMCSAs 1a-1d, respectively. Intermolecular hydrogen bonding interactions were demonstrated through theoretical calculations of enantiomers of (±)-G1 with TAMCSA 1a by means of the hybrid functional theory with the standard basis sets of 3-21G of the Gaussian 03 program.