(4S,2'S,3'R)-3-[2'-azido-3'-methoxy-3'-phenylpropionyl]-4-(1-methylethyl)-2-oxazolidinone

Base Information

• Chemical Name: (4S,2'S,3'R)-3-[2'-azido-3'-methoxy-3'-phenylpropionyl]-4-(1-methylethyl)-2-oxazolidinone
• CAS No.: 700375-94-6
• Molecular Formula: C₁₆H₂₀N₄O₄
• Molecular Weight: 332.359

Synonyms:(4S,2'S,3'R)-3-[2'-azido-3'-methoxy-3'-phenylpropionyl]-4-(1-methylethyl)-2-oxazolidinone

Chemical Property of (4S,2'S,3'R)-3-[2'-azido-3'-methoxy-3'-phenylpropionyl]-4-(1-methylethyl)-2-oxazolidinone

Chemical Property:

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Technology Process of (4S,2'S,3'R)-3-[2'-azido-3'-methoxy-3'-phenylpropionyl]-4-(1-methylethyl)-2-oxazolidinone

There total 2 articles about (4S,2'S,3'R)-3-[2'-azido-3'-methoxy-3'-phenylpropionyl]-4-(1-methylethyl)-2-oxazolidinone 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: 84.0%

(4S,2'R,3'R)-3-[2'-bromo-3'-methoxy-3'-phenylpropionyl]-4-(1-methylethyl)-2-oxazolidinone (700375-80-0) → (4S,2'S,3'R)-3-[2'-azido-3'-methoxy-3'-phenylpropionyl]-4-(1-methylethyl)-2-oxazolidinone (700375-94-6)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 60 ℃;

DOI:10.1016/j.tetasy.2005.12.014

Reference yield:

(4S)-4-isopropyl-3-[(2E)-3-phenylprop-2-enoyl]-1,3-oxazolidin-2-one (112459-60-6) → (4S,2'S,3'R)-3-[2'-azido-3'-methoxy-3'-phenylpropionyl]-4-(1-methylethyl)-2-oxazolidinone (700375-94-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 64 percent / Ag₂O; Br₂ / 0.5 h / 0 - 5 °C

2: 84 percent / NaN₃ / dimethylformamide / 60 °C

With sodium azide; bromine; silver(l) oxide; In N,N-dimethyl-formamide;

DOI:10.1016/j.tetasy.2005.12.014

Reference yield: 77.0%

(4S,2'S,3'R)-3-[2'-azido-3'-methoxy-3'-phenylpropionyl]-4-(1-methylethyl)-2-oxazolidinone (700375-94-6) → (2S,3R)-2-azido-3-methoxy-3-phenyl-propionic acid

Guidance literature:

With lithium hydroxide; dihydrogen peroxide; In tetrahydrofuran; at 0 - 5 ℃; for 2h;

DOI:10.1016/j.tetasy.2005.12.014

upstream raw materials:

(4S,2'R,3'R)-3-[2'-bromo-3'-methoxy-3'-phenylpropionyl]-4-(1-methylethyl)-2-oxazolidinone

(4S)-4-isopropyl-3-[(2E)-3-phenylprop-2-enoyl]-1,3-oxazolidin-2-one

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