[1-hydroxymethyl-2-(1H-indol-3-yl)-2-oxo-ethyl]-carbamic acid benzyl ester

Base Information

• Chemical Name: [1-hydroxymethyl-2-(1H-indol-3-yl)-2-oxo-ethyl]-carbamic acid benzyl ester
• CAS No.: 689225-39-6
• Molecular Formula: C₁₉H₁₈N₂O₄
• Molecular Weight: 338.363
• Mol file: 689225-39-6.mol

Synonyms:[1-hydroxymethyl-2-(1H-indol-3-yl)-2-oxo-ethyl]-carbamic acid benzyl ester

Chemical Property of [1-hydroxymethyl-2-(1H-indol-3-yl)-2-oxo-ethyl]-carbamic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [1-hydroxymethyl-2-(1H-indol-3-yl)-2-oxo-ethyl]-carbamic acid benzyl ester

There total 1 articles about [1-hydroxymethyl-2-(1H-indol-3-yl)-2-oxo-ethyl]-carbamic acid benzyl ester 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: 95.0%

(S)-N-benzyloxycarbonyl-L-tryptophan methyl ester (2717-76-2,130812-44-1,130812-46-3) → [1-hydroxymethyl-2-(1H-indol-3-yl)-2-oxo-ethyl]-carbamic acid benzyl ester (689225-39-6)

Guidance literature:

(S)-N-benzyloxycarbonyl-L-tryptophan methyl ester; With lithium borohydride; In tetrahydrofuran; for 1h; Heating;

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; water; at 20 ℃; for 1h; Further stages.;

DOI:10.1016/j.tetlet.2004.01.140

Reference yield: 59.0%

[1-hydroxymethyl-2-(1H-indol-3-yl)-2-oxo-ethyl]-carbamic acid benzyl ester (689225-39-6) → [2-(4-hydroxy-1H-indol-3-yl)-1-hydroxymethyl-2-oxo-ethyl]-carbamic acid benzyl ester (689225-40-9)

Guidance literature:

[1-hydroxymethyl-2-(1H-indol-3-yl)-2-oxo-ethyl]-carbamic acid benzyl ester; With thallium(III) trifluoroacetate; In trifluoroacetic acid; at 20 ℃; for 1h;

With copper(II) sulfate; In N,N-dimethyl-formamide; at 130 ℃; for 0.166667h; Further stages.;

DOI:10.1016/j.tetlet.2004.01.140

Reference yield:

[1-hydroxymethyl-2-(1H-indol-3-yl)-2-oxo-ethyl]-carbamic acid benzyl ester (689225-39-6) → N-[4-formyl-8-(2-nitro-benzenesulfonylamino)-pyrrolo[4,3,2-de]quinolin-6-yl]-acetamide (689225-50-1)

Guidance literature:

Multi-step reaction with 11 steps

1.1: Tl(OCOCF₃)3 / trifluoroacetic acid / 1 h / 20 °C

1.2: 59 percent / CuSO₄*5H₂O / dimethylformamide / 0.17 h / 130 °C

2.1: 85 percent / NaBH₃CN; BF₃*Et₂O / tetrahydrofuran / 4 h / 20 °C

3.1: 82 percent / NO(SO₃K)2 / acetone; aq. phosphate buffer / 2 h / 20 °C / pH 7

4.1: 79 percent / air / benzene / 4 h / 20 °C

5.1: 100 percent / H₂ / Pd/C / ethanol / 2 h / 20 °C

6.1: air / dimethylformamide / 1 h / 70 °C

7.1: dimethylformamide / 12 h / 20 °C

8.1: Tf₂O; pyridine / CH₂Cl₂ / 1 h / -78 °C

8.2: 68 percent / n-Bu₄NN₃ / CH₂Cl₂ / 12 h / -78 - 20 °C

9.1: H₂ / Lindlar catalyst / ethanol / 2 h / 20 °C

9.2: 75 percent / pyridine / 1,2-dichloro-ethane / 1 h / 50 °C

10.1: 100 percent / acetone; H₂O / 120 h / 20 °C

11.1: 80 percent / PCC; Al₂O₃ / acetic acid; CH₂Cl₂ / 4 h / 20 °C

With pyridine; aluminum oxide; air; potassium nitrososulfonate; trifluoromethylsulfonic anhydride; boron trifluoride diethyl etherate; hydrogen; sodium cyanoborohydride; pyridinium chlorochromate; thallium(III) trifluoroacetate; palladium on activated charcoal; Lindlar's catalyst; In tetrahydrofuran; phosphate buffer; ethanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; acetone; trifluoroacetic acid; benzene;

DOI:10.1016/j.tetlet.2004.01.140

upstream raw materials:

(S)-N-benzyloxycarbonyl-L-tryptophan methyl ester

Downstream raw materials:

[2-(4-hydroxy-1H-indol-3-yl)-1-hydroxymethyl-2-oxo-ethyl]-carbamic acid benzyl ester

[2-(4-hydroxy-1H-indol-3-yl)-1-hydroxymethyl-ethyl]-carbamic acid benzyl ester

[2-(4,7-dioxo-4,7-dihydro-1H-indol-3-yl)-1-hydroxymethyl-ethyl]-carbamic acid benzyl ester

N-[4-formyl-8-(2-nitro-benzenesulfonylamino)-pyrrolo[4,3,2-de]quinolin-6-yl]-acetamide