(R)-3-{[(benzyloxy)carbonyl]amino}-2-({1-[(tert-butoxy)carbonyl]-1H-indol-3-yl}methyl)propionic acid

Base Information

• Chemical Name: (R)-3-{[(benzyloxy)carbonyl]amino}-2-({1-[(tert-butoxy)carbonyl]-1H-indol-3-yl}methyl)propionic acid
• CAS No.: 468721-37-1
• Molecular Formula: C₂₅H₂₈N₂O₆
• Molecular Weight: 452.507

Synonyms:(R)-3-{[(benzyloxy)carbonyl]amino}-2-({1-[(tert-butoxy)carbonyl]-1H-indol-3-yl}methyl)propionic acid

Chemical Property of (R)-3-{[(benzyloxy)carbonyl]amino}-2-({1-[(tert-butoxy)carbonyl]-1H-indol-3-yl}methyl)propionic acid

Chemical Property:

Purity/Quality:

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Technology Process of (R)-3-{[(benzyloxy)carbonyl]amino}-2-({1-[(tert-butoxy)carbonyl]-1H-indol-3-yl}methyl)propionic acid

There total 10 articles about (R)-3-{[(benzyloxy)carbonyl]amino}-2-({1-[(tert-butoxy)carbonyl]-1H-indol-3-yl}methyl)propionic acid 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: 98.0%

(S)-3-[(2R)-2-({[(benzyloxy)carbonyl]amino}methyl)-3-{1-[(tert-butoxy)carbonyl]indol-3-yl}-1-oxopropyl]-4-isopropyloxazolidin-2-one (468721-43-9) → (R)-3-{[(benzyloxy)carbonyl]amino}-2-({1-[(tert-butoxy)carbonyl]-1H-indol-3-yl}methyl)propionic acid (468721-37-1)

Guidance literature:

With lithium hydroxide; dihydrogen peroxide; In tetrahydrofuran; water; at 0 ℃; for 2.5h;

DOI:10.1002/1522-2675(200206)85:6<1567::AID-HLCA1567>3.0.CO;2-T

Reference yield:

Methyl indole-3-propionate (5548-09-4) → (R)-3-{[(benzyloxy)carbonyl]amino}-2-({1-[(tert-butoxy)carbonyl]-1H-indol-3-yl}methyl)propionic acid (468721-37-1)

Guidance literature:

Multi-step reaction with 7 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

7.1: 98 percent / LiOH*H₂O; H₂O₂ / tetrahydrofuran; H₂O / 2.5 h / 0 °C

With dmap; lithium hydroxide; diphenylphosphoranyl azide; hydrogen; dihydrogen peroxide; 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:

di-tert-butyl dicarbonate (24424-99-5) → (R)-3-{[(benzyloxy)carbonyl]amino}-2-({1-[(tert-butoxy)carbonyl]-1H-indol-3-yl}methyl)propionic acid (468721-37-1)

Guidance literature:

Multi-step reaction with 7 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

7.1: 98 percent / LiOH*H₂O; H₂O₂ / tetrahydrofuran; H₂O / 2.5 h / 0 °C

With dmap; lithium hydroxide; diphenylphosphoranyl azide; hydrogen; dihydrogen peroxide; 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

upstream raw materials:

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

Methyl indole-3-propionate

di-tert-butyl dicarbonate

methyl 3-{1-[(tert-butoxy)carbonyl]-1H-indol-3-yl}propionate

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