3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, mono[(2,2-dimethyl-1-oxopropoxy)methyl] ester, (S)-

Base Information

• Chemical Name: 3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, mono[(2,2-dimethyl-1-oxopropoxy)methyl] ester, (S)-
• CAS No.: 138279-20-6
• Molecular Formula: C21H24N2O8
• Molecular Weight: 432.43
• Mol file: 138279-20-6.mol

Synonyms:

Chemical Property of 3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, mono[(2,2-dimethyl-1-oxopropoxy)methyl] ester, (S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, mono[(2,2-dimethyl-1-oxopropoxy)methyl] ester, (S)-

There total 10 articles about 3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, mono[(2,2-dimethyl-1-oxopropoxy)methyl] ester, (S)- 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: 87.0%

bis(pivaloyloxymethyl) 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate (138279-16-0) → (S)-(+)-1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-5-pivaloyloxymethoxycarbonyl-3-pyridinecarboxylic acid (138279-20-6)

Guidance literature:

With water; In di-isopropyl ether; at 20 ℃; for 48h; Product distribution; lipase AH; other enzyme, other solvent and times, other substrates, enantioselectivity;

DOI:10.1016/S0040-4039(00)60861-4

Reference yield: 83.0%

bis(pivaloyloxymethyl) 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate (138279-16-0) → (R)-1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-5-pivaloyloxymethoxycarbonyl-3-pyridinecarboxylic acid (145627-21-0) + (S)-(+)-1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-5-pivaloyloxymethoxycarbonyl-3-pyridinecarboxylic acid (138279-20-6)

Guidance literature:

With water; In di-isopropyl ether; at 25 ℃; for 35h; Yields of byproduct given. Title compound not separated from byproducts; lipase AH from Pseudomonas sp.;

DOI:10.1016/0957-4166(94)80108-8

Reference yield:

1,4-dihydro-2,6-dimethyl-4-(3'-nitrophenyl)-pyridine-3,5-dicarboxylic acid (74936-81-5) → (S)-(+)-1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-5-pivaloyloxymethoxycarbonyl-3-pyridinecarboxylic acid (138279-20-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) NaH / 1.) DMF, 0 deg C, 30 min, 2.) DMF, RT, 18 h

2: lipase AH, H₂O / diisopropyl ether / 35 h / Ambient temperature

With lipase AH; water; sodium hydride; In di-isopropyl ether;

DOI:10.1248/cpb.45.863

upstream raw materials:

bis(pivaloyloxymethyl) 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate

1,4-dihydro-2,6-dimethyl-1-methoxymethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic acid

bis(pivaloyloxymethyl) 1,4-dihydro-1-(methoxymethyl)-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate

Chloromethyl pivalate

Downstream raw materials:

(S)-(+)-methyl pivaloyloxymethyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate

(R)-5-Bromo-2,6-dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3-carboxylic acid 2,2-dimethyl-propionyloxymethyl ester

(R)-5-(5,5-Dimethyl-2-oxo-2λ⁵-[1,3,2]dioxaphosphinan-2-yl)-2,6-dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3-carboxylic acid

(R)-5-(5,5-Dimethyl-2-oxo-2λ⁵-[1,3,2]dioxaphosphinan-2-yl)-2,6-dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3-carboxylic acid 2,2-dimethyl-propionyloxymethyl ester