(2R,3S)-2-isopropyl-4-(toluene-4-sulfonyl)-morpholine-3-carboxylic acid methyl ester

Base Information

• Chemical Name: (2R,3S)-2-isopropyl-4-(toluene-4-sulfonyl)-morpholine-3-carboxylic acid methyl ester
• CAS No.: 1578156-15-6
• Molecular Formula: C₁₆H₂₃NO₅S
• Molecular Weight: 341.428

Synonyms:(2R,3S)-2-isopropyl-4-(toluene-4-sulfonyl)-morpholine-3-carboxylic acid methyl ester

Chemical Property of (2R,3S)-2-isopropyl-4-(toluene-4-sulfonyl)-morpholine-3-carboxylic acid methyl ester

Chemical Property:

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Technology Process of (2R,3S)-2-isopropyl-4-(toluene-4-sulfonyl)-morpholine-3-carboxylic acid methyl ester

There total 4 articles about (2R,3S)-2-isopropyl-4-(toluene-4-sulfonyl)-morpholine-3-carboxylic acid methyl ester 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: 65.0%

(2S,3R)-3-hydroxy-4-methyl-2-(toluene-4-sulfonylamino)-pentanoic acid methyl ester (1578156-11-2) + diphenyl(vinyl)sulfonium trifluoromethanesulfonate → (2R,3S)-2-isopropyl-4-(toluene-4-sulfonyl)-morpholine-3-carboxylic acid methyl ester (1578156-15-6)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃; for 12h;

DOI:10.1021/acs.jmedchem.7b00083

Reference yield:

(2S,3R)-2-amino-3-hydroxy-4-methyl-pentanoic acid methyl ester (87421-22-5,761344-55-2) + p-toluenesulfonyl chloride (98-59-9) → (2R,3S)-2-isopropyl-4-(toluene-4-sulfonyl)-morpholine-3-carboxylic acid methyl ester (1578156-15-6)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / dichloromethane / 2 h / 0 - 20 °C

2: triethylamine / dichloromethane / 12 h / 0 °C

With triethylamine; In dichloromethane;

Reference yield:

p-toluenesulfonyl chloride (98-59-9) → (2R,3S)-2-isopropyl-4-(toluene-4-sulfonyl)-morpholine-3-carboxylic acid methyl ester (1578156-15-6)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / dichloromethane / 20 h / 0 - 20 °C

2: triethylamine / dichloromethane / 12 h / 0 °C

With triethylamine; In dichloromethane;

DOI:10.1021/acs.jmedchem.7b00083

upstream raw materials:

(2S,3R)-2-amino-3-hydroxy-4-methyl-pentanoic acid methyl ester

p-toluenesulfonyl chloride

(2S,3R)-3-hydroxy-4-methyl-2-(toluene-4-sulfonylamino)-pentanoic acid methyl ester

Downstream raw materials:

(2R,3S)-4-[[(4R)-4-(2-chloro-4-fluoro-phenyl)-5-methoxycarbonyl-2-thiazol-2-yl-1,4-dihydropyrimidin-6-yl]methyl]-2-isopropylmorpholine-3-carboxylic acid

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