3-(3,4-Dihydroxyphenyl)-2-hydrazinyl-2-methylpropanoic acid

Base Information

• Chemical Name: 3-(3,4-Dihydroxyphenyl)-2-hydrazinyl-2-methylpropanoic acid
• CAS No.: 302-53-4
• Deprecated CAS: 14585-65-0
• Molecular Formula: C10H14 N2 O4
• Molecular Weight: 226.232
• Hs Code.: 29280000
• NSC Number: 758190,92521
• UNII: 555UP07D5N
• DSSTox Substance ID: DTXSID80860427
• Nikkaji Number: J27.602B
• Wikidata: Q27166292
• ChEMBL ID: CHEMBL1179357
• Mol file: 302-53-4.mol

Synonyms:Carbidopa;Carbidopa, (R)-Isomer;Carbidopa, (S)-Isomer;Lodosin;Lodosyn;Methyldopahydrazine;MK 485;MK 486;MK-485;MK-486;MK485;MK486

Chemical Property of 3-(3,4-Dihydroxyphenyl)-2-hydrazinyl-2-methylpropanoic acid

Chemical Property:

• Melting Point: 203-206°C
• Boiling Point: 528.7±50.0 °C(Predicted)
• PKA: 3.40±0.14(Predicted)
• PSA: 115.81000
• Density: 1.420±0.06 g/cm3(Predicted)
• LogP: 1.03810
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• XLogP3: -2.2
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 226.09535693
• Heavy Atom Count: 16
• Complexity: 261

Purity/Quality:

99%+, ^*data from raw suppliers

D,L-Carbidopa ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CC1=CC(=C(C=C1)O)O)(C(=O)O)NN
• Uses: An inhibitor of aromatic amino acid decarboxylase An inhibitor of aromatic amino acid decarboxylase.

Technology Process of 3-(3,4-Dihydroxyphenyl)-2-hydrazinyl-2-methylpropanoic acid

There total 10 articles about 3-(3,4-Dihydroxyphenyl)-2-hydrazinyl-2-methylpropanoic 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: 95.0%

(+)-2-[(1S)-1-(3,4-dimethoxybenzoyl)-2-methoxy-1-methyl-2-oxoethyl]hydrazinecarboxylic acid benzyl ester (1426847-83-7) → S(-)-carbidopa (302-53-4,14585-65-0,28860-95-9,28875-92-5,31823-41-3)

Guidance literature:

(+)-2-[(1S)-1-(3,4-dimethoxybenzoyl)-2-methoxy-1-methyl-2-oxoethyl]hydrazinecarboxylic acid benzyl ester; With boron tribromide; In dichloromethane; at -78 - 23 ℃; for 24h; Inert atmosphere;

With diethylamine; In isopropyl alcohol; enantioselective reaction;

DOI:10.1016/j.tet.2017.08.015

Reference yield: 87.0%

C14H20N2O4 → S(-)-carbidopa (302-53-4,14585-65-0,28860-95-9,28875-92-5,31823-41-3)

Guidance literature:

With hydrogenchloride; In water; at 95 ℃; for 4h;

Reference yield: 87.0%

(+)-(L)-2-(N'-cyclohexylidenehydrazino)-3-(3,4-dihydroxyphenyl)-2-methyl propionic acid methyl ester (934371-48-9) → S(-)-carbidopa (302-53-4,14585-65-0,28860-95-9,28875-92-5,31823-41-3)

Guidance literature:

(+)-(L)-2-(N'-cyclohexylidenehydrazino)-3-(3,4-dihydroxyphenyl)-2-methyl propionic acid methyl ester; With hydrogenchloride; In water;

With ammonia; In water; pH=3.5;

upstream raw materials:

(+)-(L)-2-(N'-cyclohexylidenehydrazino)-3-(3,4-dihydroxyphenyl)-2-methyl propionic acid methyl ester

carbidopa

(+)-1-[(1S)-1-(3,4-dimethoxybenzoyl)-2-methoxy-1-methyl-2-oxoethyl]-1,2-hydrazinedicarboxylic acid 1,2-di-tert-butylester

(S)-benzyl 2-(1-(3,4-dimethoxyphenyl)-3-methoxy-2-methyl-1,3-dioxopropan-2-yl)hydrazinecarboxylate

Downstream raw materials:

S(-)-carbidopa

3-(3,4-dihydroxyphenyl)-2-hydrazino-2-methylpropionic acid

C₁₁H₁₆N₂O₄

1-(3,4-dihydroxyphenyl)-2-propanone

Refernces

• 1、 -. "Method for synthesizing Carbidopa". Paragraph 0033; 0034. . Retrieved 2016/12/01.
• 2、 -. "PROCESS FOR THE PREPARATION OF CARBIDOPA". Page/Page column 21. . Retrieved 2008/06/13.