N-tert-butoxycarbonyl-4-benzyloxy-7-cyano-2-naphthylamine

Base Information

• Chemical Name: N-tert-butoxycarbonyl-4-benzyloxy-7-cyano-2-naphthylamine
• CAS No.: 178877-06-0
• Molecular Formula: C₂₃H₂₂N₂O₃
• Molecular Weight: 374.439
• Mol file: 178877-06-0.mol

Synonyms:N-tert-butoxycarbonyl-4-benzyloxy-7-cyano-2-naphthylamine

Chemical Property of N-tert-butoxycarbonyl-4-benzyloxy-7-cyano-2-naphthylamine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-tert-butoxycarbonyl-4-benzyloxy-7-cyano-2-naphthylamine

There total 7 articles about N-tert-butoxycarbonyl-4-benzyloxy-7-cyano-2-naphthylamine 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: 100.0%

4-benzyloxy-7-cyano-2-naphthalenecarboxylic acid (178877-05-9) + tert-butyl alcohol (75-65-0) → N-tert-butoxycarbonyl-4-benzyloxy-7-cyano-2-naphthylamine (178877-06-0)

Guidance literature:

With diphenylphosphoranyl azide; triethylamine; for 22h; Inert atmosphere; Reflux; Molecular sieve;

DOI:10.1002/ejoc.201000966

Reference yield:

ethyl 1-benzyloxy-6-cyano-3-naphthalenecarboxylate (178877-04-8) + tert-butyl alcohol (75-65-0) → N-tert-butoxycarbonyl-4-benzyloxy-7-cyano-2-naphthylamine (178877-06-0)

Guidance literature:

ethyl 1-benzyloxy-6-cyano-3-naphthalenecarboxylate; tert-butyl alcohol; With lithium hydroxide;

With diphenyl phosphoryl azide;

Reference yield:

7-Bromo-4-hydroxynaphthalene-2-carboxylic acid ethyl ester (178876-99-8) → N-tert-butoxycarbonyl-4-benzyloxy-7-cyano-2-naphthylamine (178877-06-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 100 percent / K₂CO₃, Bu₄NI / dimethylformamide / 11 h / 25 °C

2: 96 percent / dimethylformamide / 20 h / Heating

3: 100 percent / LiOH / tetrahydrofuran; methanol; H₂O / 25 h / 25 °C

4: 87 percent / Et₃N, diphenyl phosphorazidate / 14 h / Heating

With lithium hydroxide; diphenyl phosphoryl azide; tetra-(n-butyl)ammonium iodide; potassium carbonate; triethylamine; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide;

DOI:10.1021/jo9605298

upstream raw materials:

4-benzyloxy-7-cyano-2-naphthalenecarboxylic acid

tert-butyl alcohol

7-Bromo-4-hydroxynaphthalene-2-carboxylic acid ethyl ester

4-Acetoxy-7-bromo-naphthalene-2-carboxylic acid ethyl ester

Downstream raw materials:

5-Benzyloxy-8-cyano-1-hydroxymethyl-1,2-dihydro-benzo[e]indole-3-carboxylic acid tert-butyl ester

N-(tert-Butyloxycarbonyl)-N-(2-propenyl)-4-benzyloxy-7-cyano-1-iodo-2-naphthylamine

N-(tert-Butyloxycarbonyl)-N-(formylmethyl)-4-benzyloxy-1-bromo-7-cyano-2-naphthylamine

N-(tert-Butyloxycarbonyl)-N-(3-methyl-2-buten-1-yl)-4-benzyloxy-1-bromo-7-cyano-2-naphthylamine

Refernces

• 1、 -. "Cyclopropylindole derivatives". Page/Page column 33-35. . Retrieved 2010/02/12.
• 2、 Boger, Dale L.,Han, Nianhe,Tarby, Christine M.,Boyce, Christopher W.,Cai, Hui,Jin, Qing,Kitos, Paul A.. "Synthesis, chemical properties, and preliminary evaluation of substituted CBI analogs of CC-1065 and the duocarmycins incorporating the 7-cyano-1,2,9,9a-tetrahydrocyclopropa[c]benz[e]indol-4-one alkylation subunit: Hammett quantitation of the magnitude of electronic effects on functional reactivity". . p. 4894 - 4912. Retrieved 2007/10/03.