(2S,5S)-5-((5-(6-((4-fluoro-3-methoxybenzyl)carbamoyl)-2-methylpyrimidin-4-yl)-2H-tetrazol-2-yl)methyl)-1,4-dioxane-2-carboxylic acid

Base Information

• Chemical Name: (2S,5S)-5-((5-(6-((4-fluoro-3-methoxybenzyl)carbamoyl)-2-methylpyrimidin-4-yl)-2H-tetrazol-2-yl)methyl)-1,4-dioxane-2-carboxylic acid
• CAS No.: 1112170-12-3
• Molecular Formula: C₂₁H₂₂FN₇O₆
• Molecular Weight: 487.447
• Mol file: 1112170-12-3.mol

Synonyms:(2S,5S)-5-((5-(6-((4-fluoro-3-methoxybenzyl)carbamoyl)-2-methylpyrimidin-4-yl)-2H-tetrazol-2-yl)methyl)-1,4-dioxane-2-carboxylic acid

Chemical Property of (2S,5S)-5-((5-(6-((4-fluoro-3-methoxybenzyl)carbamoyl)-2-methylpyrimidin-4-yl)-2H-tetrazol-2-yl)methyl)-1,4-dioxane-2-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,5S)-5-((5-(6-((4-fluoro-3-methoxybenzyl)carbamoyl)-2-methylpyrimidin-4-yl)-2H-tetrazol-2-yl)methyl)-1,4-dioxane-2-carboxylic acid

There total 11 articles about (2S,5S)-5-((5-(6-((4-fluoro-3-methoxybenzyl)carbamoyl)-2-methylpyrimidin-4-yl)-2H-tetrazol-2-yl)methyl)-1,4-dioxane-2-carboxylic 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: 37.0%

N-(4-fluoro-3-methoxybenzyl)-6-(2-(((2S,5R)-5-(hydroxymethyl)-1,4-dioxan-2-yl)methyl)-2H-tetrazol-5-yl)-2-methylpyrimidine-4-carboxamide (1112169-64-8) → (2S,5S)-5-((5-(6-((4-fluoro-3-methoxybenzyl)carbamoyl)-2-methylpyrimidin-4-yl)-2H-tetrazol-2-yl)methyl)-1,4-dioxane-2-carboxylic acid (1112170-12-3)

Guidance literature:

With dipyridinium dichromate; In N,N-dimethyl-formamide; at 20 ℃; for 36h;

DOI:10.1021/acs.jmedchem.5b01434

Reference yield:

rac-((2R*,5R*)-5-(hydroxymethyl)-1,4-dioxan-2-yl)methyl 4-methylbenzenesulfonate → (2S,5S)-5-((5-(6-((4-fluoro-3-methoxybenzyl)carbamoyl)-2-methylpyrimidin-4-yl)-2H-tetrazol-2-yl)methyl)-1,4-dioxane-2-carboxylic acid (1112170-12-3)

Guidance literature:

Multi-step reaction with 3 steps

1: chiral SFC(AD-H) / dichloromethane; methanol / Resolution of racemate

2: triethylamine / N,N-dimethyl acetamide / 18 h / 85 °C

3: dipyridinium dichromate / N,N-dimethyl-formamide / 36 h / 20 °C

With dipyridinium dichromate; triethylamine; In methanol; dichloromethane; N,N-dimethyl acetamide; N,N-dimethyl-formamide;

DOI:10.1021/acs.jmedchem.5b01434

Reference yield:

trans-2,5-bis-(hydroxymethyl)-1,4-dioxane (87133-52-6,452055-83-3) → (2S,5S)-5-((5-(6-((4-fluoro-3-methoxybenzyl)carbamoyl)-2-methylpyrimidin-4-yl)-2H-tetrazol-2-yl)methyl)-1,4-dioxane-2-carboxylic acid (1112170-12-3)

Guidance literature:

Multi-step reaction with 4 steps

1: triethylamine / dichloromethane / 20 - 35 °C / Inert atmosphere

2: chiral SFC(AD-H) / dichloromethane; methanol / Resolution of racemate

3: triethylamine / N,N-dimethyl acetamide / 18 h / 85 °C

4: dipyridinium dichromate / N,N-dimethyl-formamide / 36 h / 20 °C

With dipyridinium dichromate; triethylamine; In methanol; dichloromethane; N,N-dimethyl acetamide; N,N-dimethyl-formamide;

DOI:10.1021/acs.jmedchem.5b01434

upstream raw materials:

N-(4-fluoro-3-methoxybenzyl)-6-(2-(((2S,5R)-5-(hydroxymethyl)-1,4-dioxan-2-yl)methyl)-2H-tetrazol-5-yl)-2-methylpyrimidine-4-carboxamide

trans-2,5-bis-(hydroxymethyl)-1,4-dioxane

((2R,5R)-5-(hydroxymethyl)-1,4-dioxan-2-yl)methyl 4-methylbenzenesulfonate

2,4-dichloro-2-methylpyrimidine