(2S,3S)-4-((4-Chlorophenyl)amino)-2,3-dihydroxy-4-oxobutanoic acid

Base Information

• Chemical Name: (2S,3S)-4-((4-Chlorophenyl)amino)-2,3-dihydroxy-4-oxobutanoic acid
• CAS No.: 46834-56-4
• Molecular Formula: C10H10 Cl N O5
• Molecular Weight: 259.64
• European Community (EC) Number: 674-008-3
• Mol file: 46834-56-4.mol

Synonyms:46834-56-4;(2S,3S)-4-((4-Chlorophenyl)amino)-2,3-dihydroxy-4-oxobutanoic acid;(-)-4'-Chlorotartranilic acid;(2S,3S)-4-(4-chloroanilino)-2,3-dihydroxy-4-oxobutanoic acid;d-pcta;(-)-4'-chloro-tartranilic acid;WBA83456;(2S,3S)-4-(4-chlorophenylamino)-2,3-dihydroxy-4-oxobutanoic acid;MFCD00070634;AKOS022186267;DS-7795;CS-0157475;D83186;A827105;(2s,3s)-N-(4-chlorophenyl)-2,3-dihydroxy-succinamic acid;(2S,3S)-4-((4-Chlorophenyl)amino)-2,3-dihydroxy-4-oxobutanoicacid;Butanoic acid,4-[(4-chlorophenyl)amino]-2,3-dihydroxy-4-oxo-,(2S,3S)-;(2S,3S)-4-[(4-chlorophenyl)amino]-2,3-bis(oxidanyl)-4-oxidanylidene-butanoic acid;Butanoic acid, 4-[(4-chlorophenyl)amino]-2,3-dihydroxy-4-oxo-,[S-(R*,R*)]-

Chemical Property of (2S,3S)-4-((4-Chlorophenyl)amino)-2,3-dihydroxy-4-oxobutanoic acid

Chemical Property:

• Melting Point: 193-195oC (dec.)
• Boiling Point: 609.1oC at 760 mmHg
• Flash Point: 322.2oC
• PSA: 106.86000
• Density: 1.644g/cm3
• LogP: 0.15790
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 259.0247501
• Heavy Atom Count: 17
• Complexity: 290

Purity/Quality:

98%,99%, ^*data from raw suppliers

(-)-4'-Chlorotartranilic acid ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

Useful:

• Canonical SMILES: C1=CC(=CC=C1NC(=O)C(C(C(=O)O)O)O)Cl
• Isomeric SMILES: C1=CC(=CC=C1NC(=O)[C@H]([C@@H](C(=O)O)O)O)Cl

Technology Process of (2S,3S)-4-((4-Chlorophenyl)amino)-2,3-dihydroxy-4-oxobutanoic acid

There total 3 articles about (2S,3S)-4-((4-Chlorophenyl)amino)-2,3-dihydroxy-4-oxobutanoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 65.0%

(3S,4S)-2,5-dioxotetrahydrofuran-3,4-diyl diacetate (70728-23-3) + 4-chloro-aniline (106-47-8) → (2S,3S)-3-[(4-chlorophenyl)carbamoyl]-2,3-dihydroxypropanoic acid (46834-56-4)

Guidance literature:

In dichloromethane; for 15h; Heating;

DOI:10.1016/0040-4020(95)00285-G

Reference yield:

diacetyl D-(-)-tartaric acid + 4-chloro-aniline (106-47-8) → (2S,3S)-3-[(4-chlorophenyl)carbamoyl]-2,3-dihydroxypropanoic acid (46834-56-4)

Guidance literature:

In dichloromethane; for 12h; Reflux;

Reference yield:

(2S,3S)-2,3-Diacetoxy-N-(4-chloro-phenyl)-succinamic acid → (2S,3S)-3-[(4-chlorophenyl)carbamoyl]-2,3-dihydroxypropanoic acid (46834-56-4)

Guidance literature:

With potassium hydroxide;

upstream raw materials:

(3S,4S)-2,5-dioxotetrahydrofuran-3,4-diyl diacetate

4-chloro-aniline

Downstream raw materials:

(R)-(+)-5-(4-amino-3-methylphenyl)-8-methyl-8,9-dihydro-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepine salt with L-tartaric acid semi-4-chloroanilide

Refernces

• 1、 Huh, Nam,Thompson, Charles M.. "Enantioenriched N-(2-Chloroalkyl)-3-acetoxypiperidines as Potential Cholinotoxic Agents. Synthesis and Preliminary Evidence for Spirocyclic Aziridinium Formation.". . p. 5935 - 5950. Retrieved 2007/10/02.