(S-(R*,R*))-3-((o-Aminophenyl)thio)-3-(p-methoxyphenyl)lactic acid

Base Information

• Chemical Name: (S-(R*,R*))-3-((o-Aminophenyl)thio)-3-(p-methoxyphenyl)lactic acid
• CAS No.: 42399-48-4
• Molecular Formula: C16H17 N O4 S
• Molecular Weight: 319.381
• Hs Code.: 2930909090
• European Community (EC) Number: 255-798-5
• DSSTox Substance ID: DTXSID80195201
• Nikkaji Number: J305.013K
• Wikidata: Q83068077
• Mol file: 42399-48-4.mol

Synonyms:42399-48-4;(S-(R*,R*))-3-((o-Aminophenyl)thio)-3-(p-methoxyphenyl)lactic acid;(2S,3S)-3-(2-aminophenyl)sulfanyl-2-hydroxy-3-(4-methoxyphenyl)propanoic acid;EINECS 255-798-5;30193-57-8;(alphaS,betaS)-beta-[(2-Aminophenyl)thio]-alpha-hydroxy-4-methoxybenzenepropanoic acid;C16H17NO4S;[S-(R*,R*)]-3-[(o-aminophenyl)thio]-3-(p-methoxyphenyl)lactic acid;(2S,3S)-3-(2-Amino-phenylsulfanyl)-;SCHEMBL7425966;DTXSID80195201;KHQWPNQLSKDWAR-CABCVRRESA-N;AKOS015962830;(2S,3S)-3-(2-AMINO-PHENYLSULFANYL)-2-HYDROXY-3-(4-METHOXY-PHENYL)-PROPIONIC ACID;AC-18736;(2S,3S)-2-hydroxy-3-(4-methoxyphenyl)-3-(2-aminophenylthio)propionic acid

Chemical Property of (S-(R*,R*))-3-((o-Aminophenyl)thio)-3-(p-methoxyphenyl)lactic acid

Chemical Property:

• Vapor Pressure: 4.92E-12mmHg at 25°C
• Boiling Point: 529.3°Cat760mmHg
• Flash Point: 273.9°C
• PSA: 118.08000
• Density: 1.37g/cm³
• LogP: 3.13750
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 319.08782920
• Heavy Atom Count: 22
• Complexity: 360

Purity/Quality:

98%Min ^*data from raw suppliers

(αS,βS)-β-[(2-Aminophenyl)thio]-α-hydroxy-4-methoxybenzenepropanoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)C(C(C(=O)O)O)SC2=CC=CC=C2N
• Isomeric SMILES: COC1=CC=C(C=C1)[C@@H]([C@H](C(=O)O)O)SC2=CC=CC=C2N
• Uses: (αS,βS)-β-[(2-Aminophenyl)thio]-α-hydroxy-4-methoxybenzenepropanoic Acid is used in the synthesis of Diltiazem (D460620), a calcium channel blocher with vasodilating activity. Antianginal; antihypertensive; antiarrhythmic (class IV).

Technology Process of (S-(R*,R*))-3-((o-Aminophenyl)thio)-3-(p-methoxyphenyl)lactic acid

There total 36 articles about (S-(R*,R*))-3-((o-Aminophenyl)thio)-3-(p-methoxyphenyl)lactic 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: 81.0%

(αS,βS,1R,2S)-β-<(2-aminophenyl)thio>-α-hydroxy-β-(4-methoxyphenyl)propanoic acid 2-phenylcyclohexyl ester hydrochloride (138382-02-2) → (2S,3S)-threo-2-hydroxy-3-(2-aminophenylthio)-3-(4-methoxyphenyl)-propionic acid (42399-48-4)

Guidance literature:

With sodium hydroxide; In ethanol; water; for 2h; Heating;

DOI:10.1021/jo00029a013

Reference yield: 56.0%

(2S,3S)-isopropyl 3-<(2-aminophenyl)thio>-2-hydroxy-3-(4-methoxyphenyl)propionate (157019-57-3) → (2S,3S)-threo-2-hydroxy-3-(2-aminophenylthio)-3-(4-methoxyphenyl)-propionic acid (42399-48-4)

Guidance literature:

With sodium hydroxide; In ethanol; water; for 1h; Heating;

DOI:10.1016/S0040-4020(01)89369-8

Reference yield:

C26H35NO4S → (2S,3S)-threo-2-hydroxy-3-(2-aminophenylthio)-3-(4-methoxyphenyl)-propionic acid (42399-48-4)

Guidance literature:

With potassium hydroxide; In water; at 40 ℃; for 2h;

upstream raw materials:

(2S,3R)-2-Acetoxy-3-chloro-3-(4-methoxy-phenyl)-propionic acid methyl ester

potassium o-aminobenzenethiolate

(+)-(2S,3S)-2-hydroxy-3-(4-methoxyphenyl)-3-(2-aminophenylthio)propanoic acid methyl ester

(αS,βS,1R,2S)-β-<(2-aminophenyl)thio>-α-hydroxy-β-(4-methoxyphenyl)propanoic acid 2-phenylcyclohexyl ester hydrochloride

Downstream raw materials:

2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one

(2S,3S)-3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one

water

diltiazem hydrochloride

Refernces

• 1、 Jacobsen, Eric N.,Deng, Li,Furukawa, Yoshiro,Martinez, Luis E.. "Enantioselective Catalytic Epoxidation of Cinnamate Esters". . p. 4323 - 4334. Retrieved 2007/10/02.
• 2、 Schwartz,Madan,Mohacsi,O'Brien,Todaro,Coffen. "Enantioselective synthesis of calcium channel blockers of the diltiazem group". . p. 851 - 856. Retrieved 2007/10/02.