benzyl (R)-3-({1-[(tert-butoxy)carbonyl]-1H-indol-3-yl}methyl)-4-[(S)-4-isopropyl-2-oxooxazolidin-3-yl]-4-oxobutanoate

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Chemical Name:benzyl (R)-3-({1-[(tert-butoxy)carbonyl]-1H-indol-3-yl}methyl)-4-[(S)-4-isopropyl-2-oxooxazolidin-3-yl]-4-oxobutanoate
CAS No.:468721-40-6
Molecular Formula:C₃₁H₃₆N₂O₇
Molecular Weight:548.636
Hs Code.:

Synonyms:benzyl (R)-3-({1-[(tert-butoxy)carbonyl]-1H-indol-3-yl}methyl)-4-[(S)-4-isopropyl-2-oxooxazolidin-3-yl]-4-oxobutanoate

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Chemical Property of benzyl (R)-3-({1-[(tert-butoxy)carbonyl]-1H-indol-3-yl}methyl)-4-[(S)-4-isopropyl-2-oxooxazolidin-3-yl]-4-oxobutanoate

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Technology Process of benzyl (R)-3-({1-[(tert-butoxy)carbonyl]-1H-indol-3-yl}methyl)-4-[(S)-4-isopropyl-2-oxooxazolidin-3-yl]-4-oxobutanoate

There total 5 articles about benzyl (R)-3-({1-[(tert-butoxy)carbonyl]-1H-indol-3-yl}methyl)-4-[(S)-4-isopropyl-2-oxooxazolidin-3-yl]-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: 76.0%

: 468721-39-3
(S)-3-(3-{1-[(tert-butoxy)carbonyl]-1H-indol-3-yl}-1-oxopropyl)-4-isopropyloxazolidin-2-one

: 5437-45-6
Benzyl bromoacetate

: 468721-40-6
benzyl (R)-3-({1-[(tert-butoxy)carbonyl]-1H-indol-3-yl}methyl)-4-[(S)-4-isopropyl-2-oxooxazolidin-3-yl]-4-oxobutanoate

Guidance literature:: (S)-3-(3-{1-[(tert-butoxy)carbonyl]-1H-indol-3-yl}-1-oxopropyl)-4-isopropyloxazolidin-2-one; With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.833333h;

Benzyl bromoacetate; In tetrahydrofuran; at -78 ℃; for 3h;
DOI:10.1002/1522-2675(200206)85:6<1567::AID-HLCA1567>3.0.CO;2-T

Reference yield:

: 5548-09-4
Methyl indole-3-propionate

: 468721-40-6
benzyl (R)-3-({1-[(tert-butoxy)carbonyl]-1H-indol-3-yl}methyl)-4-[(S)-4-isopropyl-2-oxooxazolidin-3-yl]-4-oxobutanoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 92 percent / DMAP / acetonitrile / 2.5 h / 20 °C

2.1: 94 percent / LiOH*H₂O / tetrahydrofuran; H₂O / 9 h / 20 °C

3.1: pivaloyl chloride; Et₃N / tetrahydrofuran / 1.5 h / -30 °C

3.2: 83 percent / LiCl / tetrahydrofuran / 11 h / -30 - 20 °C

4.1: NaHMDS / tetrahydrofuran / 0.83 h / -78 °C

4.2: 76 percent / tetrahydrofuran / 3 h / -78 °C

With dmap; lithium hydroxide; sodium hexamethyldisilazane; pivaloyl chloride; triethylamine; In tetrahydrofuran; water; acetonitrile;
DOI:10.1002/1522-2675(200206)85:6<1567::AID-HLCA1567>3.0.CO;2-T

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 468721-40-6
benzyl (R)-3-({1-[(tert-butoxy)carbonyl]-1H-indol-3-yl}methyl)-4-[(S)-4-isopropyl-2-oxooxazolidin-3-yl]-4-oxobutanoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 92 percent / DMAP / acetonitrile / 2.5 h / 20 °C

2.1: 94 percent / LiOH*H₂O / tetrahydrofuran; H₂O / 9 h / 20 °C

3.1: pivaloyl chloride; Et₃N / tetrahydrofuran / 1.5 h / -30 °C

3.2: 83 percent / LiCl / tetrahydrofuran / 11 h / -30 - 20 °C

4.1: NaHMDS / tetrahydrofuran / 0.83 h / -78 °C

4.2: 76 percent / tetrahydrofuran / 3 h / -78 °C

With dmap; lithium hydroxide; sodium hexamethyldisilazane; pivaloyl chloride; triethylamine; In tetrahydrofuran; water; acetonitrile;
DOI:10.1002/1522-2675(200206)85:6<1567::AID-HLCA1567>3.0.CO;2-T