(R)-4-methoxy-2-methyl-4-oxobutanoic acid

Base Information

• Chemical Name: (R)-4-methoxy-2-methyl-4-oxobutanoic acid
• CAS No.: 81025-83-4
• Molecular Formula: C₆H₁₀O₄
• Molecular Weight: 146.143
• Hs Code.: 2918990090
• DSSTox Substance ID: DTXSID50423220
• Nikkaji Number: J84.166H
• Wikidata: Q82235375
• Mol file: 81025-83-4.mol

Synonyms:(R)-4-methoxy-2-methyl-4-oxobutanoic acid;81025-83-4;(R)-(+)-2-Methylsuccinic acid 4-methyl ester;(2R)-4-methoxy-2-methyl-4-oxobutanoic acid;MFCD00211259;(R)-(+)-3-Methylsuccinic Acid 1-Monomethyl Ester;SCHEMBL1183661;DTXSID50423220;UVQYBUYGFBXQGO-SCSAIBSYSA-N;4-Methyl hydrogen (R)-methylsuccinate;AKOS006378566;DS-17873;(R)-2-methyl-succinic acid 4-methyl ester;(R)-4-Methoxy-2-methyl-4-oxobutanoicacid;(R)-4-methoxy-2-methyl-4-oxobutyric acid;(2R)-methylsuccinic acid 4-monomethyl ester;CS-0186135;C76592;(R)-Butanedioic acid, 2-methyl, 4-methyl ester;(R)-2-METHYLSUCCINIC ACID 4-METHYL ESTER;(R)-(+)-2-Methylsuccinic acid 4-methyl ester, 95%;(R)?-?(+)?-?2-?Methylsuccinic acid 4-methyl ester

Chemical Property of (R)-4-methoxy-2-methyl-4-oxobutanoic acid

Chemical Property:

• Vapor Pressure: 0.00758mmHg at 25°C
• Refractive Index: n20/D 1.4320(lit.)
• Boiling Point: 241-242 °C760 mm Hg(lit.)
• Flash Point: 101 °F
• PSA: 63.60000
• Density: 1.150 g/mL at 25 °C(lit.)
• LogP: 0.27020
• Storage Temp.: Refrigerator
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 146.05790880
• Heavy Atom Count: 10
• Complexity: 141

Purity/Quality:

99%, ^*data from raw suppliers

(R)-(+)-2-MethylsuccinicAcid4-MethylEster ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 10-36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CC(=O)OC)C(=O)O
• Isomeric SMILES: C[C@H](CC(=O)OC)C(=O)O
• Uses: (R)-(+)-2-Methylsuccinic Acid 4-Methyl Ester is used in the preparation of triazole-containing macrocycles.

Technology Process of (R)-4-methoxy-2-methyl-4-oxobutanoic acid

There total 17 articles about (R)-4-methoxy-2-methyl-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: 100.0%

4-methoxy-2-methylene-4-oxobutanoic acid (7338-27-4) → (R)-2-methyl-succinic acid 4-methyl ester (23268-03-3,80986-16-9,111266-27-4,81025-83-4) + (2S)-4-methoxy-2-methyl-4-oxobutanoic acid (111266-27-4)

Guidance literature:

With hydrogen; triethylamine; Ru₂Cl₄((R)-(+)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl)2; In tetrahydrofuran; toluene; at 35 ℃; for 24h; under 2206.5 Torr; Title compound not separated from byproducts; op = 60percent, var. cat. RuHCl*2<(+)-BINAP>;

DOI:10.1016/S0040-4039(00)96006-4

Reference yield: 99.0%

4-methoxy-2-methylene-4-oxobutanoic acid (7338-27-4) → (R)-2-methyl-succinic acid 4-methyl ester (23268-03-3,80986-16-9,111266-27-4,81025-83-4)

Guidance literature:

With catASium; hydrogen; In dichloromethane; for 48h; under 3000.3 Torr; enantioselective reaction; Autoclave; Inert atmosphere;

DOI:10.1002/chem.201202701

Reference yield: 99.0%

→ (R)-2-methyl-succinic acid 4-methyl ester (23268-03-3,80986-16-9,111266-27-4,81025-83-4)

Guidance literature:

With C₅₄H₆₈IrNP⁽¹⁺⁾*C₃₂H₁₂BF₂₄^(1-); hydrogen; caesium carbonate; In methanol; at 45 ℃; for 0.25h; under 4500.45 Torr; Glovebox; Sealed tube;

upstream raw materials:

(R)-methylsuccinic acid dimethyl ester

4-methoxy-2-methylene-4-oxobutanoic acid

methyl 2-methylsuccinate

methanol

Downstream raw materials:

(R)-3-methyl-4-oxo-4-(3-(trifluoromethyl)benzylamino)butyric acid methyl ester

C₂₂H₂₉N₅O₄

methyl 4-(2-{4-[({2-[(3-{[(2-{[(2R)-4-methoxy-2-methyl-4-oxobutanoyl](methyl)amino}ethyl)(pentan-3-yl)amino]methyl}benzoyl)amino]-4,5,6,7-tetrahydro-1-benzothiophen-3-yl}carbonyl)amino]phenyl}ethyl)benzoate

Refernces

• 1、 Poklukar, Ga?per,Stephan, Michel,Mohar, Barbara. "Modular 1,1′-Ferrocenediyl-cored P-Stereogenic Diphosphines: ′′JDayPhos′′ Series and its Use in Rhodium(I)-Catalyzed Hydrogenation". supporting information. p. 2566 - 2570. Retrieved 2018/05/16.
• 2、 Shibata, Takanori,Michino, Masamichi,Kurita, Hisaki,Tahara, Yu-Ki,Kanyiva, Kyalo Stephen. "Enantioselective Formal C?H Conjugate Addition of Acetanilides to β-Substituted Acrylates by Chiral Iridium Catalysts". supporting information. p. 88 - 91. Retrieved 2017/01/09.