(1R,2R)-2-(methoxycarbonyl)-4-oxocyclopentanecarboxylic acid

Base Information

• Chemical Name: (1R,2R)-2-(methoxycarbonyl)-4-oxocyclopentanecarboxylic acid
• CAS No.: 1445591-99-0
• Molecular Formula: C₈H₁₀O₅
• Molecular Weight: 186.164
• Mol file: 1445591-99-0.mol

Synonyms:(1R,2R)-2-(methoxycarbonyl)-4-oxocyclopentanecarboxylic acid

Chemical Property of (1R,2R)-2-(methoxycarbonyl)-4-oxocyclopentanecarboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2R)-2-(methoxycarbonyl)-4-oxocyclopentanecarboxylic acid

There total 1 articles about (1R,2R)-2-(methoxycarbonyl)-4-oxocyclopentanecarboxylic 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:

(+/-)-trans-4-oxo-1,2-cyclopentanedicarboxylic acid bis(methyl ester) (6453-07-2,28269-02-5,28269-03-6,35079-19-7,74500-50-8,115794-30-4) → (1R,2R)-2-(methoxycarbonyl)-4-oxocyclopentanecarboxylic acid (1445591-99-0) + (+)-(1S,2S)-dimethyl-4-oxocyclopentane 1,2-dicarboxylate (115794-30-4) + trans-(1R,2R)-1,2-Bis(methoxycarbonyl)-4-oxocyclopentane (35079-19-7) + (1S,2S)-2-(methoxycarbonyl)-4-oxocyclopentanecarboxylic acid (115694-82-1)

Guidance literature:

With Aminoacylase from Aspergillus sp; In aq. phosphate buffer; at 15 - 20 ℃; for 16h; pH=7; Reagent/catalyst; Temperature; Resolution of racemate; Enzymatic reaction;

Reference yield: 67.0%

(1R,2R)-2-(methoxycarbonyl)-4-oxocyclopentanecarboxylic acid (1445591-99-0) + benzyl chloroformate (501-53-1,94274-21-2) → (1R,2R)-1-benzyl 2-methyl 4-oxocyclopentane-1,2-dicarboxylate (1445592-00-6,164916-54-5)

Guidance literature:

(1R,2R)-2-(methoxycarbonyl)-4-oxocyclopentanecarboxylic acid; benzyl chloroformate; With triethylamine; In dichloromethane; at 0 ℃; for 0.0833333h;

With dmap; In dichloromethane; at 0 ℃; for 0.666667h;

Reference yield:

(1R,2R)-2-(methoxycarbonyl)-4-oxocyclopentanecarboxylic acid (1445591-99-0) → (7R,8R)-methyl 8-(5-(4-bromophenyl)-1H-imidazol-2-yl)-1,4-dioxaspiro[4.4]nonane-7-carboxylate (1445592-02-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: triethylamine / dichloromethane / 0.08 h / 0 °C

1.2: 0.67 h / 0 °C

2.1: toluene-4-sulfonic acid / toluene / 4 h / Reflux; Dean-Stark

3.1: hydrogen; palladium 10% on activated carbon / methanol / 25 °C

4.1: acetonitrile / 5 h / 20 °C / Inert atmosphere

5.1: ammonium acetate / 5,5-dimethyl-1,3-cyclohexadiene / 2 h / Dean-Stark; Reflux

With palladium 10% on activated carbon; ammonium acetate; hydrogen; toluene-4-sulfonic acid; triethylamine; In methanol; 5,5-dimethyl-1,3-cyclohexadiene; dichloromethane; toluene; acetonitrile;

upstream raw materials:

(+/-)-trans-4-oxo-1,2-cyclopentanedicarboxylic acid bis(methyl ester)

Downstream raw materials:

(1R,2R)-1-benzyl 2-methyl 4-oxocyclopentane-1,2-dicarboxylate

methyl ((2S)-3-methyl-1-(2-(5-(4-(2-((7S,8S)-8-((R)-3-methylmorpholine-4-carbonyl)-1,4-dioxaspiro[4.4]nonan-7-yl)-1H-imidazol-5-yl)-[1,1‘-biphenyl]-4-yl)-1H-imidazol-2-yl)pyrrolidin-1-yl)-1-oxobutan-2-yl)carbamate

(7R,8R)-7-benzyl 8-methyl 1,4-dioxaspiro[4.4]nonane-7,8-dicarboxylate

(7R,8R)-methyl 8-(5-(4-bromophenyl)-1H-imidazol-2-yl)-1,4-dioxaspiro[4.4]nonane-7-carboxylate