(E)-3-[(2S,4S,5R)-3-(2-Iodo-acetyl)-4-methyl-5-phenyl-oxazolidin-2-yl]-acrylic acid methyl ester

Base Information

• Chemical Name: (E)-3-[(2S,4S,5R)-3-(2-Iodo-acetyl)-4-methyl-5-phenyl-oxazolidin-2-yl]-acrylic acid methyl ester
• CAS No.: 143060-05-3
• Molecular Formula: C₁₆H₁₈INO₄
• Molecular Weight: 415.228

Synonyms:(E)-3-[(2S,4S,5R)-3-(2-Iodo-acetyl)-4-methyl-5-phenyl-oxazolidin-2-yl]-acrylic acid methyl ester

Chemical Property of (E)-3-[(2S,4S,5R)-3-(2-Iodo-acetyl)-4-methyl-5-phenyl-oxazolidin-2-yl]-acrylic acid methyl ester

Chemical Property:

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Technology Process of (E)-3-[(2S,4S,5R)-3-(2-Iodo-acetyl)-4-methyl-5-phenyl-oxazolidin-2-yl]-acrylic acid methyl ester

There total 5 articles about (E)-3-[(2S,4S,5R)-3-(2-Iodo-acetyl)-4-methyl-5-phenyl-oxazolidin-2-yl]-acrylic 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: 90.0%

(E)-3-[(2S,4S,5R)-3-(2-Chloro-acetyl)-4-methyl-5-phenyl-oxazolidin-2-yl]-acrylic acid methyl ester (143060-10-0) → (E)-3-[(2S,4S,5R)-3-(2-Iodo-acetyl)-4-methyl-5-phenyl-oxazolidin-2-yl]-acrylic acid methyl ester (143060-05-3)

Guidance literature:

With sodium iodide; In acetone; for 1h; Ambient temperature;

DOI:10.1016/S0040-4020(01)88474-X

Reference yield:

(1R,2S)-norephedrine (492-41-1,58550-13-3,757124-50-8) → (E)-3-[(2S,4S,5R)-3-(2-Iodo-acetyl)-4-methyl-5-phenyl-oxazolidin-2-yl]-acrylic acid methyl ester (143060-05-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 92 percent / 2N NaOH / H₂O / Ambient temperature; pH ca. 7

2: 80 percent / pyridinium tosylate / benzene / 70 h / Heating

3: 90 percent / NaI / acetone / 1 h / Ambient temperature

With sodium hydroxide; pyridinium p-toluenesulfonate; sodium iodide; In water; acetone; benzene;

DOI:10.1016/S0040-4020(01)88474-X

Reference yield:

monofumaraldehyde dimethylacetal monomethylester (32815-00-2) → (E)-3-[(2S,4S,5R)-3-(2-Iodo-acetyl)-4-methyl-5-phenyl-oxazolidin-2-yl]-acrylic acid methyl ester (143060-05-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / pyridinium tosylate / benzene / 70 h / Heating

2: 90 percent / NaI / acetone / 1 h / Ambient temperature

With pyridinium p-toluenesulfonate; sodium iodide; In acetone; benzene;

DOI:10.1016/S0040-4020(01)88474-X

upstream raw materials:

monofumaraldehyde dimethylacetal monomethylester

(1S,2R)-(+)-2-chloro-N-(2-hydroxy-1-methyl-2-phenylethyl)acetamide

(E)-3-[(2S,4S,5R)-3-(2-Chloro-acetyl)-4-methyl-5-phenyl-oxazolidin-2-yl]-acrylic acid methyl ester

(1R,2S)-norephedrine

Downstream raw materials:

(2R,3S,6R,7R,7aS)-3,6,7-Trimethyl-2-phenyl-tetrahydro-pyrrolo[2,1-b]oxazol-5-one

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