30925-11-2

Basic information

• Product Name: Boc-N-Methyl-L-phenylglycine
• Synonyms: BOC-N-ALPHA-METHYL-L-PHENYLGLYCINE;BOC-MEPHG-OH;BOC-N-METHYL-L-PHENYLGLYCINE;BOC-N-ME-PHENYLGLYCINE;BOC-N-ME-PHG-OH;BOC-L-MEPHG-OH;BOC-(PH)SAR-OH;N-ALPHA-(T-BUTYLOXYCARBONYL)-N-ALPHA-METHYL-L-PHENYLGLYCINE
• CAS NO: 30925-11-2
• Molecular Formula: C₁₄H₁₉NO₄
• Molecular Weight: 265.3
• Product Categories: PROTECTED AMINO ACID & PEPTIDES;N-Methyl Amino Acids;Boc-Amino acid series
• Mol File: 30925-11-2.mol

Chemical Properties

• Melting Point: 118.9-124.4°C
• Boiling Point: 384.6 °C at 760 mmHg
• Flash Point: 186.4 °C
• Appearance: /Solid
• Density: 1.166 g/cm³
• Vapor Pressure: 1.33E-06mmHg at 25°C
• Refractive Index: 1.533
• Storage Temp.: Store at RT.
• PKA: 3.53±0.10(Predicted)
• CAS DataBase Reference: Boc-N-Methyl-L-phenylglycine(CAS DataBase Reference)
• NIST Chemistry Reference: Boc-N-Methyl-L-phenylglycine(30925-11-2)
• EPA Substance Registry System: Boc-N-Methyl-L-phenylglycine(30925-11-2)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 30925-11-2(Hazardous Substances Data)

Usage

Chemical Properties

White powder

InChI:InChI=1/C14H19NO4/c1-14(2,3)19-13(18)15(4)11(12(16)17)10-8-6-5-7-9-10/h5-9,11H,1-4H3,(H,16,17)/t11-/m0/s1

Upstream product

• 2900-27-8 (2S)-2-[(tert-butoxycarbonyl)amino]-2-phenylethanoic acid 
• 74-88-4 methyl iodide 
• 124-38-9 carbon dioxide 
• 81616-14-0 tert-butyl N-benzyl-N-methylcarbamate 
• 2935-35-5 (S)-2-phenylglycine 
• 58632-95-4 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile 
• 24424-99-5 di-tert-butyl dicarbonate 

Downstream Products

• 145963-02-6 Boc-(NMe)Phg-Asp(OBzl)-1Nal-NH₂ 
• 220122-65-6 N-<(2'S)-methylamino-2'-phenylethyl>-(3R,4R)-dimethyl-4-(3-hydroxyphenyl)piperidine 
• 146075-39-0 Boc-(NMe)Chg-OH 
• 145963-03-7 Boc-(NMe)Chg-Asp(OBzl)-1Nal-NH₂ 
• 136092-91-6 N-methyl-L-phenyl-Gly-L-Trp-ol 
• 136093-00-0 (-)-indolactam-Phg 
• 1145835-55-7 (S)-2-[(2-1H-indol-3-ylacetyl)methylamino]-N-(4-isopropyl-phenyl)-2-phenylacetamide 
• 1208094-50-1 [(4-hydroxymethylphenylcarbamoyl)phenylmethyl]methylcarbamic acid tert-butyl ester 
• 1361409-74-6 C₂₀H₂₃N₅O₃ 
• 1374333-12-6 C₁₅H₁₅FN₂O 
• 1361409-71-3 (S)-2-(2-(1H-indol-3-yl)-N-methylacetamido)-N-(4-fluorophenyl)-2-phenylacetamide 
• 1361409-73-5 (S)-tert-butyl2-(4-fluorophenylamino)-2-oxo-1-phenylethyl-(methyl)carbamate 

Relevant articles and documents

COMPOUNDS HAVING ACTIVITY IN INCREASING ION TRANSPORT BY MUTANT-CFTR AND USES THEREOF

The invention provides compositions, pharmaceutical preparations and methods for increasing activity of a mutant cystic fibrosis transmembrane conductance regulator protein (mutant-CFTR). The compositions pharmaceutical preparations and methods are useful for the study and treatment of disorders associated with mutant-CFTR, such as cystic fibrosis. The compositions and pharmaceutical preparations of the invention may comprise one or more phenylglycine-containing compounds of the invention, or an analog or derivative thereof

Rapid access to N-Boc phenylglycine derivatives via benzylic lithiation reactions

We report a novel and efficient method for the enantioselective synthesis of N-Boc protected phenylglycines. Yields and enantiomeric ratios vary widely depending on the nature of the solvent, the substrate and on the method of forming the chiral complex. Results show that the major reaction pathway is an enantioselective deprotonation/substitution process. The enantioselectivity appears to be limited by the chiral discrimination ability of the s-BuLi-(-)-sparteine complex. The synthetic method described is one of the shortest route to useful enantioenriched N-Boc phenylglycine derivatives.

An expedient enantioselective synthesis of N-t-Boc-protected phenylsarcosine

Herein we describe a novel approach to the asymmetric synthesis of N-t-Boc-phenylsarcosine. The synthesis involves the enantioselective deprotonation at the benzylic position of N-t-Boc-N-methylbenzylamine 2 using the chiral complex s-BuLi/(-) sparteine 1

CCK-B agonist or antagonist activities of structurally hindered and peptidase-resistant Boc-CCK4 derivatives

Replacement of Met31 by (N-Me)Nle in CCK8 or CCK4 has been shown to improve the affinity and selectivity for CCK-B receptors. In order to obtain molecules with enhanced bioavailability, two novel series of protected tetrapeptides of the general formula Boc-Trp30-X-Asp-Y33 have been developed. Introduction of (N-Me)Nle and the bulky, aromatic naphthylalaninamide (Nal-NH2) in positions X and Y, respectively, does not greatly modify the affinity for guinea pig brain CCK-B receptors. In contrast, incorporation of hindering N-methyl amino acids such as (N-Me)Phe, (N-Me)Phg, or (N-Me)Chg, but not their non-methylated counterparts, in position X induced a large decrease in affinity for the CCK-B binding sites. Among the various peptides synthesized, Boc-[(N-Me)Nle31,1Nal- NH233]CCK4 (2) (K(I) = 2.8 nM), Boc-[Phg31,1Nal-NH233]CCK4 (15) (K(I) = 14 nM), and Boc-[Phg31,1Nal-N(CH3)233]CCK4 (17) (K(I) = 39 nM) displayed good affinities for brain CCK-B receptors and had good selectivity ratios. These pseudopeptides, in which the presence of unnatural and hydrophobic residues is expected to improve their penetration of the central nervous system, were shown to be very resistant to brain peptidases. Interestingly, whereas compounds 2 and 15 proved to be full agonists for rat hippocampal CCK-B receptors when measured in an electrophysiological assay, compound 17 behaved as a potent antagonist in the same test and displayed a good affinity in rat brain K(I)(CCK-B) = 51 nM as compared to the Merck antagonist L365,260, K(I)(CCK-B) = 12 nM. This illustrates a simple means to obtain CCK-B antagonists and suggests that the free, CONH2 group plays a critical role in the recognition of the agonist state of brain CCK-B receptors.

Synthesis of new indolactam analogues by microbial conversion

Ten indolactam congeners with L-Ala, Abu, γ,δ-Δ-Nva, Nva, Nle, tert-Leu, Leu, Ile, allo-Ile. Phg instead ofL-Val in (-)-indolactam-Val, were synthesized from their seco-compounds (N-methyl-L-amino acidyl-L-tryptophonol) by microbial conversion.