(S)-tert-butyl 3-[3-tert-butoxy-2-(diphenylmethyleneamino)-3-oxopropyl]-4-iodo-1H-indole-1-carboxylate

Base Information

• Chemical Name: (S)-tert-butyl 3-[3-tert-butoxy-2-(diphenylmethyleneamino)-3-oxopropyl]-4-iodo-1H-indole-1-carboxylate
• CAS No.: 956469-17-3
• Molecular Formula: C₃₃H₃₅IN₂O₄
• Molecular Weight: 650.556
• Mol file: 956469-17-3.mol

Synonyms:(S)-tert-butyl 3-[3-tert-butoxy-2-(diphenylmethyleneamino)-3-oxopropyl]-4-iodo-1H-indole-1-carboxylate

Chemical Property of (S)-tert-butyl 3-[3-tert-butoxy-2-(diphenylmethyleneamino)-3-oxopropyl]-4-iodo-1H-indole-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-tert-butyl 3-[3-tert-butoxy-2-(diphenylmethyleneamino)-3-oxopropyl]-4-iodo-1H-indole-1-carboxylate

There total 5 articles about (S)-tert-butyl 3-[3-tert-butoxy-2-(diphenylmethyleneamino)-3-oxopropyl]-4-iodo-1H-indole-1-carboxylate 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: 97.0%

3-bromomethyl-4-iodo-indole-1-carboxylic acid tert-butyl ester (956469-16-2) + N-(diphenylmethylene)glycine tert-butyl ester (81477-94-3) → (S)-tert-butyl 3-[3-tert-butoxy-2-(diphenylmethyleneamino)-3-oxopropyl]-4-iodo-1H-indole-1-carboxylate (956469-17-3)

Guidance literature:

With potassium hydroxide; In dichloromethane; toluene; at 0 ℃; for 8h;

DOI:10.1021/jo071162h

Reference yield:

4-iodo-indole-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester (956469-14-0) → (S)-tert-butyl 3-[3-tert-butoxy-2-(diphenylmethyleneamino)-3-oxopropyl]-4-iodo-1H-indole-1-carboxylate (956469-17-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 78.4 percent / DIBAL-H / CH₂Cl₂ / 0.67 h / 0 °C

2: 80.3 percent / PBr₃ / CH₂Cl₂ / 0.67 h / 0 °C

3: 97 percent / cinchona alkaloid-derived quaternary ammonium salt; aq. KOH / CH₂Cl₂; toluene / 8 h / 0 °C

With potassium hydroxide; phosphorus tribromide; diisobutylaluminium hydride; In dichloromethane; toluene;

DOI:10.1021/jo071162h

Reference yield:

3-hydroxymethyl-4-iodo-indole-1-carboxylic acid tert-butyl ester (956469-15-1) → (S)-tert-butyl 3-[3-tert-butoxy-2-(diphenylmethyleneamino)-3-oxopropyl]-4-iodo-1H-indole-1-carboxylate (956469-17-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 80.3 percent / PBr₃ / CH₂Cl₂ / 0.67 h / 0 °C

2: 97 percent / cinchona alkaloid-derived quaternary ammonium salt; aq. KOH / CH₂Cl₂; toluene / 8 h / 0 °C

With potassium hydroxide; phosphorus tribromide; In dichloromethane; toluene;

DOI:10.1021/jo071162h

upstream raw materials:

3-bromomethyl-4-iodo-indole-1-carboxylic acid tert-butyl ester

N-(diphenylmethylene)glycine tert-butyl ester

4-iodo-indole-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester

3-hydroxymethyl-4-iodo-indole-1-carboxylic acid tert-butyl ester

Downstream raw materials:

(-)-trans-clavicipitic acid