(S)-3-[(2R)-2-({[(benzyloxy)carbonyl]amino}methyl)-3-{1-[(tert-butoxy)carbonyl]indol-3-yl}-1-oxopropyl]-4-isopropyloxazolidin-2-one

Base Information

Chemical Name:(S)-3-[(2R)-2-({[(benzyloxy)carbonyl]amino}methyl)-3-{1-[(tert-butoxy)carbonyl]indol-3-yl}-1-oxopropyl]-4-isopropyloxazolidin-2-one
CAS No.:468721-43-9
Molecular Formula:C₃₁H₃₇N₃O₇
Molecular Weight:563.651
Hs Code.:

Synonyms:(S)-3-[(2R)-2-({[(benzyloxy)carbonyl]amino}methyl)-3-{1-[(tert-butoxy)carbonyl]indol-3-yl}-1-oxopropyl]-4-isopropyloxazolidin-2-one

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Chemical Property of (S)-3-[(2R)-2-({[(benzyloxy)carbonyl]amino}methyl)-3-{1-[(tert-butoxy)carbonyl]indol-3-yl}-1-oxopropyl]-4-isopropyloxazolidin-2-one

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Technology Process of (S)-3-[(2R)-2-({[(benzyloxy)carbonyl]amino}methyl)-3-{1-[(tert-butoxy)carbonyl]indol-3-yl}-1-oxopropyl]-4-isopropyloxazolidin-2-one

There total 9 articles about (S)-3-[(2R)-2-({[(benzyloxy)carbonyl]amino}methyl)-3-{1-[(tert-butoxy)carbonyl]indol-3-yl}-1-oxopropyl]-4-isopropyloxazolidin-2-one 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: 74.0%

: 100-51-6,185532-71-2
benzyl alcohol

: 468721-41-7
(R)-3-({1-[(tert-butoxy)carbonyl]-1H-indol-3-yl}methyl)-4-[(S)-4-isopropyl-2-oxooxazolidin-3-yl]-4-oxobutyric acid

: 468721-43-9
(S)-3-[(2R)-2-({[(benzyloxy)carbonyl]amino}methyl)-3-{1-[(tert-butoxy)carbonyl]indol-3-yl}-1-oxopropyl]-4-isopropyloxazolidin-2-one

Guidance literature:: With diphenylphosphoranyl azide; triethylamine; In toluene; for 1h; Heating;
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

: 468721-43-9
(S)-3-[(2R)-2-({[(benzyloxy)carbonyl]amino}methyl)-3-{1-[(tert-butoxy)carbonyl]indol-3-yl}-1-oxopropyl]-4-isopropyloxazolidin-2-one

Guidance literature:: Multi-step reaction with 6 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

5.1: 100 percent / H₂ / Pd/C / tetrahydrofuran / 4 h

6.1: 74 percent / diphenylphosphoryl azide; Et₃N / toluene / 1 h / Heating

With dmap; lithium hydroxide; diphenylphosphoranyl azide; hydrogen; sodium hexamethyldisilazane; pivaloyl chloride; triethylamine; palladium on activated charcoal; In tetrahydrofuran; water; toluene; 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

: 468721-43-9
(S)-3-[(2R)-2-({[(benzyloxy)carbonyl]amino}methyl)-3-{1-[(tert-butoxy)carbonyl]indol-3-yl}-1-oxopropyl]-4-isopropyloxazolidin-2-one

Guidance literature:: Multi-step reaction with 6 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

5.1: 100 percent / H₂ / Pd/C / tetrahydrofuran / 4 h

6.1: 74 percent / diphenylphosphoryl azide; Et₃N / toluene / 1 h / Heating

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