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

Base Information

• Chemical Name: (2R,3R)-4-((4-Chlorophenyl)amino)-2,3-dihydroxy-4-oxobutanoic acid
• CAS No.: 17447-35-7
• Molecular Formula: C10H10 Cl N O5
• Molecular Weight: 259.646
• Hs Code.: 2924299090
• European Community (EC) Number: 673-687-3
• DSSTox Substance ID: DTXSID20938513
• Wikidata: Q76146291
• Mol file: 17447-35-7.mol

Synonyms:17447-35-7;(+)-4'-Chlorotartranilic acid;(2R,3R)-4-((4-Chlorophenyl)amino)-2,3-dihydroxy-4-oxobutanoic acid;(2R,3R)-4-(4-chloroanilino)-2,3-dihydroxy-4-oxobutanoic acid;l-pcta;4-(4-Chloroanilino)-2,3-dihydroxy-4-oxobutanoic acid;SCHEMBL18137202;DTXSID20938513;JLBJYGCSAOHRPK-HTQZYQBOSA-N;MFCD00021698;AKOS000277292;CS-0333866;A811641;(2R,3R)-4-(4-chloroanilino)-2,3-dihydroxy-4-oxo-butanoic acid;(2R,3R)-4-(4-chlorophenylamino)-2,3-dihydroxy-4-oxobutanoic acid;(2R,3R)-3-[(4-CHLOROPHENYL)CARBAMOYL]-2,3-DIHYDROXYPROPANOIC ACID;(2R,3R)-4-((4-Chlorophenyl)amino)-2,3-dihydroxy-4-oxobutanoicacid;Butanoic acid,4-[(4-chlorophenyl)amino]-2,3-dihydroxy-4-oxo-,(2R,3R)-

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

Chemical Property:

• Melting Point: 193 °C
• Boiling Point: 609.1°Cat760mmHg
• Flash Point: 322.2°C
• PSA: 106.86000
• Density: 1.644g/cm³
• LogP: 0.15790
• Storage Temp.: 2-8°C
• 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:

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:

SDS file from LookChem

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

There total 2 articles about (2R,3R)-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: 68.0%

4-chloro-aniline (106-47-8) + (3R-trans)-dihydro-2,5-dioxofuran-3,4-diyl diacetate (6283-74-5) → (R,R)-(+)-4-chlorotartranilic acid (17447-35-7)

Guidance literature:

In dichloromethane; for 15h; Heating;

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

Reference yield: 52.0%

→ (R,R)-(+)-4-chlorotartranilic acid (17447-35-7)

Guidance literature:

Reference yield: 92.0%

2-(3-ethoxy-4-methoxyphenyl)-1-(methylsulfonyl)eth-2-ylamine (253168-94-4) + (R,R)-(+)-4-chlorotartranilic acid (17447-35-7) → C12H19NO4S*C10H10ClNO5

Guidance literature:

With hydrogenchloride; In water; at 60 - 70 ℃; Solvent; Resolution of racemate; Heating;

upstream raw materials:

4-chloro-aniline

(3R-trans)-dihydro-2,5-dioxofuran-3,4-diyl diacetate

Downstream raw materials:

(S)-(-)-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

Apremilast

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.