ethyl 2-cyano-2-(5-benzyloxy-1-ethoxycarbonyl-1H-indol-3-yl)acetate

Base Information

• Chemical Name: ethyl 2-cyano-2-(5-benzyloxy-1-ethoxycarbonyl-1H-indol-3-yl)acetate
• CAS No.: 190182-63-9
• Molecular Formula: C₂₃H₂₂N₂O₅
• Molecular Weight: 406.438
• Mol file: 190182-63-9.mol

Synonyms:ethyl 2-cyano-2-(5-benzyloxy-1-ethoxycarbonyl-1H-indol-3-yl)acetate

Chemical Property of ethyl 2-cyano-2-(5-benzyloxy-1-ethoxycarbonyl-1H-indol-3-yl)acetate

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

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Technology Process of ethyl 2-cyano-2-(5-benzyloxy-1-ethoxycarbonyl-1H-indol-3-yl)acetate

There total 1 articles about ethyl 2-cyano-2-(5-benzyloxy-1-ethoxycarbonyl-1H-indol-3-yl)acetate 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: 75.6%

NSC 73391 (2436-15-9) + Diethyl carbonate (105-58-8,76619-83-5) → ethyl 2-cyano-2-(5-benzyloxy-1-ethoxycarbonyl-1H-indol-3-yl)acetate (190182-63-9)

Guidance literature:

With sodium; at 90 - 105 ℃; for 2.5h; Na adding insmall portions to a soln. of the indole in (EtO)2CO at 90 deg C; stirring 2 h at 105 deg C; evapg.;

DOI:10.1111/j.2042-7158.1997.tb06789.x

Reference yield: 76.5%

acetic anhydride (108-24-7) + ethyl 2-cyano-2-(5-benzyloxy-1-ethoxycarbonyl-1H-indol-3-yl)acetate (190182-63-9) → ethyl 3-acetamido-2-(5-benzyloxy-1-ethoxycarbonyl-1H-indol-3-yl)propanoate

Guidance literature:

With hydrogen; Raney-Ni W-2; at 21 ℃; for 8h; under 2585.74 Torr; in the excess of Ac₂O;

DOI:10.1111/j.2042-7158.1997.tb06789.x

Reference yield:

ethyl 2-cyano-2-(5-benzyloxy-1-ethoxycarbonyl-1H-indol-3-yl)acetate (190182-63-9) → methyl 3-amino-2-(5-(benzyloxy)-1H-indol-3-yl)propanoate hydrochloride

Guidance literature:

Multi-step reaction with 3 steps

1: 76.5 percent / H₂ / Raney-Ni W-2 / 8 h / 21 °C / 2585.74 Torr / in the excess of Ac₂O

2: 63.2 percent / aq. NaOH / 8 h / refluxing under Ar; diluting with H₂O; acidifying with AcOH up to pH 6.12; ppt. collecting by vacuum filtration

3: 77.6 percent / SOCl₂; HCl / methanol; dioxane / 18 h / -10 - 21 °C / SOCl₂ adding to a pre-cooled susp. of the acid in MeOH, stirring under Ar, evapg., treated with aq. K₂CO₃ and with 4 N HCl

With hydrogenchloride; sodium hydroxide; thionyl chloride; hydrogen; Raney-Ni W-2; In 1,4-dioxane; methanol; 1: Reduction / 2: Hydrolysis / 3: Esterification;

DOI:10.1111/j.2042-7158.1997.tb06789.x

upstream raw materials:

NSC 73391

Diethyl carbonate

Downstream raw materials:

3-amino-2-(5-benzyloxy-1-ethoxycarbonyl-1H-indol-3-yl)propanoic acid