tert-butyl 4-[(4R)-2-oxo-4-benzyl(1,3-oxazolidin-3-yl)](3S)-3-[(4-chlorophenyl)methyl]-4-oxobutanoate

Base Information

• Chemical Name: tert-butyl 4-[(4R)-2-oxo-4-benzyl(1,3-oxazolidin-3-yl)](3S)-3-[(4-chlorophenyl)methyl]-4-oxobutanoate
• CAS No.: 494783-50-5
• Molecular Formula: C₂₅H₂₈ClNO₅
• Molecular Weight: 457.954

Synonyms:tert-butyl 4-[(4R)-2-oxo-4-benzyl(1,3-oxazolidin-3-yl)](3S)-3-[(4-chlorophenyl)methyl]-4-oxobutanoate

Chemical Property of tert-butyl 4-[(4R)-2-oxo-4-benzyl(1,3-oxazolidin-3-yl)](3S)-3-[(4-chlorophenyl)methyl]-4-oxobutanoate

Chemical Property:

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Technology Process of tert-butyl 4-[(4R)-2-oxo-4-benzyl(1,3-oxazolidin-3-yl)](3S)-3-[(4-chlorophenyl)methyl]-4-oxobutanoate

There total 2 articles about tert-butyl 4-[(4R)-2-oxo-4-benzyl(1,3-oxazolidin-3-yl)](3S)-3-[(4-chlorophenyl)methyl]-4-oxobutanoate 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: 75.0%

bromoacetic acid tert-butyl ester (5292-43-3) + (4R)-3-[3-(4-chlorophenyl)propanoyl]-4-benzyl-1,3-oxazolidin-2-one (494783-49-2) → tert-butyl 4-[(4R)-2-oxo-4-benzyl(1,3-oxazolidin-3-yl)](3S)-3-[(4-chlorophenyl)methyl]-4-oxobutanoate (494783-50-5)

Guidance literature:

With potassium hexamethylsilazane; In tetrahydrofuran; at -78 ℃;

DOI:10.1016/j.bmcl.2003.10.056

Reference yield:

3-(4-chlorophenyl)propanoyl chloride (52085-96-8) → tert-butyl 4-[(4R)-2-oxo-4-benzyl(1,3-oxazolidin-3-yl)](3S)-3-[(4-chlorophenyl)methyl]-4-oxobutanoate (494783-50-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / tetrahydrofuran / -78 °C

2: 75 percent / KHMDS / tetrahydrofuran / -78 °C

With potassium hexamethylsilazane; In tetrahydrofuran;

DOI:10.1016/j.bmcl.2003.10.056

Reference yield:

tert-butyl 4-[(4R)-2-oxo-4-benzyl(1,3-oxazolidin-3-yl)](3S)-3-[(4-chlorophenyl)methyl]-4-oxobutanoate (494783-50-5) → (2S)-3-[(tert-Butyl)-oxycarbonyl]-2-[(4-chlorophenyl)methyl]-propanoic acid (494783-51-6)

Guidance literature:

With lithium hydroxide; dihydrogen peroxide; In tetrahydrofuran; at 0 ℃;

DOI:10.1016/j.bmcl.2003.10.056

upstream raw materials:

bromoacetic acid tert-butyl ester

(4R)-3-[3-(4-chlorophenyl)propanoyl]-4-benzyl-1,3-oxazolidin-2-one

3-(4-chlorophenyl)propanoyl chloride

Downstream raw materials:

(2S)-3-[(tert-Butyl)-oxycarbonyl]-2-[(4-chlorophenyl)methyl]-propanoic acid

(3S)-3-[(4-Chlorophenyl)-methyl]-4-(4-{2-[(cyclopropylmethyl)-(methylsulfonyl)-amino]phenyl}piperazinyl)-4-oxobutanoic acid

tert-butyl (3S)-3-[(4-chlorophenyl)-methyl]-4-(4-{2-[(cyclopropylmethyl)(methylsulfonyl)-amino]phenyl}-piperazinyl)-4-oxobutanoate

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