148554-82-9

Usage

Uses

Used in Pharmaceutical Industry:
(+/-)-α-<(methoxycarbonyl)amino>benzenebutanoic acid is used as an analgesic for relieving pain, such as headaches and muscle aches. It is also used as an antipyretic to reduce fever and as an anti-inflammatory agent to alleviate inflammation.
Used in Treatment of Arthritis:
In the field of rheumatology, (+/-)-α-<(methoxycarbonyl)amino>benzenebutanoic acid is used as a treatment for various types of arthritis, including osteoarthritis and rheumatoid arthritis, to help manage pain and inflammation.
Used in Relief of Menstrual Cramps:
(+/-)-α-<(methoxycarbonyl)amino>benzenebutanoic acid is used as a medication to alleviate the pain and discomfort associated with menstrual cramps.
It is important to use (+/-)-α-<(methoxycarbonyl)amino>benzenebutanoic acid as directed, as it can cause side effects such as stomach irritation and an increased risk of heart attack or stroke, especially when used at high doses or for long periods of time.

Upstream product

• 1012-05-1 D,L-homophenylalanine 
• 79-22-1 methyl chloroformate 
• 152660-49-6 (S)-2-(N-methoxycarbonyl amino)-4-oxo-4-phenyl butyric acid 
• 79686-90-1 N-(methoxycarbonyl)aspartic anhydride 
• 71-43-2 benzene 
• 136978-25-1 -2-(methoxycarbonyl)amino-4-phenyl-3-butenoic acid 
• 128885-39-2 (S)-4-Hydroxy-2-methoxycarbonylamino-4-phenyl-butyric acid 
• 943-73-7 D-homophenylalanine 
• 288068-75-7 (Z)-2-Methoxycarbonylamino-4-phenyl-but-2-enoic acid 
• 64920-29-2 2-oxo-4-phenylbutanoic acid ethyl ester 
• 90878-19-6 phenethylmagnesium chloride 
• 288068-74-6 (Z)-2-Methoxycarbonylamino-4-phenyl-but-2-enoic acid ethyl ester 
• 591-50-4 iodobenzene 
• 136978-32-0 (S)-N-(Methoxycarbonyl)-O-(p-toluenesulfonyl)serine Benzyl Ester 

Downstream Products

• 1349904-25-1 (S)-methyl [1-{ethyl(phenyl)amino}-1-oxo-4-phenylbutan-2-yl]carbamate 
• 137037-60-6 (S)-2-<(Methoxycarbonyl)amino>-4-phenylbutanoic Acid Methyl Ester 

Relevant academic research and scientific papers

ANTI-VIRAL COMPOUNDS

Compounds effective in inhibiting replication of Hepatitis C virus (“HCV”) are described. This invention also relates to processes of making such compounds, compositions comprising such compounds, and methods of using such compounds to treat HCV infection.

Synthesis of optically active N-aryl amino acid derivatives through the asymmetric petasis reaction catalyzed by a novel hydroxy-thiourea catalyst

Thiourea makes peptides: Asymmetric Petasis reactions with vinylboronates and α-iminoamides are effectively catalyzed by the novel hydroxy-thiourea catalyst 1 (up to 86% yield, 93% ee; see scheme). This reaction can be applied not only to the synthesis of

Anti-Viral Compounds

Compounds effective in inhibiting replication of Hepatitis C virus (“HCV”) are described. This invention also relates to processes of making such compounds, compositions comprising such compounds, and methods of using such compounds to treat HCV infection.

Lysine sulfonamides as novel HIV-protease inhibitors: Nε-Acyl aromatic α-amino acids

A series of lysine sulfonamide analogues bearing Nε-acyl aromatic amino acids were synthesized using an efficient synthetic route. Evaluation of these novel protease inhibitors revealed compounds with high potency against wild-type and multiple-protease inhibitor-resistant HIV viruses.

An efficient synthesis of chiral homophenylalanine derivatives via enantioselective hydrogenation

Chiral homophenylalanine derivatives were synthesized via enantioselective hydrogenation of 5a and 5b catalyzed by rhodium complexes bearing chiral phosphine and phosphinite legands. Enantiomeric excesses up to 96.2% were achieved when S-spiroOP(S-1) was used as a chiral ligand under 500 psi of H2 pressure in acetone.

Novel stereoselective syntheses of the fused benzazepine dopamine D1 antagonist (6as,13br)-11-chloro-6,6a,7,8,9,13b-hexahydro-7-methyl-5h-benzo[d]naphth[2,1-b] azepin-12-ol (sch 39166): 2. l-homophenylalanine-based syntheses

Two enantioselective syntheses of the fused benzazepine dopamine D1 antagonist (6aS,13bR)-11-chloro-6,6a,7,8,9,13b-hexahydro-7-methyl-5H-benzo[d]naphth[2,1-b] azepin-12-ol (1) are described in which the starting material is (+)-L-homophenylalan

Synthesis of optically active (2-arylvinyl)glycine derivatives by palladium-catalyzed arylation of (s)-n-(benzyloxycarbonyl)vinylglycine

Phenyl, tolyl, anisyl, and 1-naphthyl iodides (7a-g,n) smoothly reacted with (S)-N-(benzyloxycarbonyl)-vinylglycine (6) in H2O in the presence of Pd(OAc)2, Bu4NCI, and NaHCO3 at 45°C, producing [S-(E)]-(2- arylvinyl)glycine derivatives 8a-g, n of high enantiomeric purity. The yields of the reactions of 3- (7f), 2- (7e), and 4-iodoanisoles (7g) increased in this order. This relationship between the yield and the position of substitution has been found to hold for bromophenyl iodides (7i-k), although somewhat lower chemical and optical yields were realized in these cases. Phenyl iodide 71 carrying an electron-withdrawing 4-acetyl group gave an unsatisfactory result, and more electron-deficient 4-nitrophenyl iodide (7m) did not provide the desired product. All these results suggest that the reaction is advantageous with electron-sufficient substrates 7. However, this was not the case for 4-iodophenol (7h), as well as some heterocyclic iodides.

New silane reduction of aromatic ketones mediated by titanium tetrachloride : A synthesis of γ- and δ-aryl substituted amino acids

Several N-protected 4-aryl-2-aminobutanoic acids (γ-aryl substituted amino acids ; 7a-f) and N-protected 5-aryl-2-aminopentanoic acids (δ-aryl substituted amino acids ; 8a,b and d) were prepared in good yields by reduction of the corresponding aromatic or heteroaromatic ketones (3 and 4) with triethylsilane (Et3SiH) or dimethylphenylsilane (PhMe2SiH) in the presence of titanium tetrachloride (TiCl4), respectively. The reduction proceeded without racemization and was successfully applied to the synthesis of optically active γ-and δ-aryl substituted amino acids (14a and 15a).

Reduction of Aromatic Ketones into Methylenes Using Triethylsilane and Titanium Tetrachloride. Synthesis of 2-Aminobutanoic Acids

Several N-protected 2-aminobutanoic acids (3) with aromatic or heteroaromatic ring at their terminal position were prepared in good yields by reduction of the corresponding ketones (1) with triethylsilane (Et3SiH) in the presence of titanium tetrachloride

Wittig reaction with N-protected 3-(triphenylphosphonio)alaninates: Synthesis of optically active (E)-(2-arylvinyl)glycine derivatives

(R)-[2-Carboxy-2-[(methoxycarbonyl)amino]ethyl]triphenylphosphonium chloride (1) was converted by treatment with anion exchange resin (HCO3-) into the inner salt 13h, which gave a better yield (43%) than 1 in the Wittig reaction with benzaldehyde to afford the [S-(E)]-(2-phenylvinyl)glycine derivative 24. The inner salt 13i bearing an N-benzyioxycarbonyl group was prepared by hydrogenolysis of (R)-[3-benzyloxy-2-[(benzyloxycarbonyl)amino]-3-oxopropyl]triphenylpho sphonium chloride (11e) over palladium on carbon, followed by dehydrochlorination. Hydrogenolysis of 11e over Pearlman's catalyst afforded the unprotected phosphonium chloride 12 (X = Cl). N-tert-Butoxycarbonylation of 12 followed by dehydrochlorination afforded 13j, which was more efficiently prepared through hydrogenolysis of (R)-[3-benzyloxy-2-[(tert-butoxycarbonyl)amino]-3-oxopropyl]triphenylp hosphonium chloride (11f). The usefulness of 13h-j as building blocks for the synthesis of configurationally labile (2-arylvinyl)glycine derivatives was exemplihed by the Wittig reactions with piperonal, which exclusively afforded the (E)-isomers 18h-j with high optical purity in 28-39% yield.