2-[N-(tert-Butyloxycarbonyl)-N-(3-tetrahydropyranyloxy-2-propen-1-yl)]amino-4-benzyloxy-1-bromo-7-cyanonaphthalene

Base Information

• Chemical Name: 2-[N-(tert-Butyloxycarbonyl)-N-(3-tetrahydropyranyloxy-2-propen-1-yl)]amino-4-benzyloxy-1-bromo-7-cyanonaphthalene
• CAS No.: 200351-81-1
• Molecular Formula: C₃₁H₃₃BrN₂O₅
• Molecular Weight: 593.517
• Mol file: 200351-81-1.mol

Synonyms:2-[N-(tert-Butyloxycarbonyl)-N-(3-tetrahydropyranyloxy-2-propen-1-yl)]amino-4-benzyloxy-1-bromo-7-cyanonaphthalene

Chemical Property of 2-[N-(tert-Butyloxycarbonyl)-N-(3-tetrahydropyranyloxy-2-propen-1-yl)]amino-4-benzyloxy-1-bromo-7-cyanonaphthalene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[N-(tert-Butyloxycarbonyl)-N-(3-tetrahydropyranyloxy-2-propen-1-yl)]amino-4-benzyloxy-1-bromo-7-cyanonaphthalene

There total 10 articles about 2-[N-(tert-Butyloxycarbonyl)-N-(3-tetrahydropyranyloxy-2-propen-1-yl)]amino-4-benzyloxy-1-bromo-7-cyanonaphthalene 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:

7-Bromo-4-hydroxynaphthalene-2-carboxylic acid ethyl ester (178876-99-8) → 2-[N-(tert-Butyloxycarbonyl)-N-(3-tetrahydropyranyloxy-2-propen-1-yl)]amino-4-benzyloxy-1-bromo-7-cyanonaphthalene (200351-81-1)

Guidance literature:

Multi-step reaction with 8 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

5: 87 percent / NBS, H₂SO₄ / tetrahydrofuran / 4 h / -60 °C

6: 1) NaH / 1) DMF, 25 deg C, 30 min, 2) DMF, 0 deg C, 1 h; 25 deg C, overnight

7: 1) O₃/O₂, 2) dimethyl sulfide / 1) CH₃OH, CH₂Cl₂, -78 deg C, 72 s, 2) CH₃OH, CH₂Cl₂, -78 deg C -> 25 deg C; 25 deg C, 5 h

8: 1) n-BuLi, 2) HMPA / 1) THF, hexane, -78 deg C, 10 min; -78 deg C -> 0 deg C, 20 min, 2) THF, -78 deg C, 1.5 h; 25 deg C, 24 h

With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium hydroxide; N-Bromosuccinimide; n-butyllithium; dimethylsulfide; sulfuric acid; diphenyl phosphoryl azide; oxygen; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; ozone; triethylamine; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide;

DOI:10.1021/jo9605298

Reference yield:

4-Acetoxy-7-bromo-naphthalene-2-carboxylic acid ethyl ester (178877-00-4) → 2-[N-(tert-Butyloxycarbonyl)-N-(3-tetrahydropyranyloxy-2-propen-1-yl)]amino-4-benzyloxy-1-bromo-7-cyanonaphthalene (200351-81-1)

Guidance literature:

Multi-step reaction with 9 steps

1: 100 percent / K₂CO₃ / ethanol / 1 h / Heating

2: 100 percent / K₂CO₃, Bu₄NI / dimethylformamide / 11 h / 25 °C

3: 96 percent / dimethylformamide / 20 h / Heating

4: 100 percent / LiOH / tetrahydrofuran; methanol; H₂O / 25 h / 25 °C

5: 87 percent / Et₃N, diphenyl phosphorazidate / 14 h / Heating

6: 87 percent / NBS, H₂SO₄ / tetrahydrofuran / 4 h / -60 °C

7: 1) NaH / 1) DMF, 25 deg C, 30 min, 2) DMF, 0 deg C, 1 h; 25 deg C, overnight

8: 1) O₃/O₂, 2) dimethyl sulfide / 1) CH₃OH, CH₂Cl₂, -78 deg C, 72 s, 2) CH₃OH, CH₂Cl₂, -78 deg C -> 25 deg C; 25 deg C, 5 h

9: 1) n-BuLi, 2) HMPA / 1) THF, hexane, -78 deg C, 10 min; -78 deg C -> 0 deg C, 20 min, 2) THF, -78 deg C, 1.5 h; 25 deg C, 24 h

With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium hydroxide; N-Bromosuccinimide; n-butyllithium; dimethylsulfide; sulfuric acid; diphenyl phosphoryl azide; oxygen; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; ozone; triethylamine; In tetrahydrofuran; methanol; ethanol; water; N,N-dimethyl-formamide;

DOI:10.1021/jo9605298

Reference yield:

4-benzyloxy-7-cyano-2-naphthalenecarboxylic acid (178877-05-9) → 2-[N-(tert-Butyloxycarbonyl)-N-(3-tetrahydropyranyloxy-2-propen-1-yl)]amino-4-benzyloxy-1-bromo-7-cyanonaphthalene (200351-81-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 87 percent / Et₃N, diphenyl phosphorazidate / 14 h / Heating

2: 87 percent / NBS, H₂SO₄ / tetrahydrofuran / 4 h / -60 °C

3: 1) NaH / 1) DMF, 25 deg C, 30 min, 2) DMF, 0 deg C, 1 h; 25 deg C, overnight

4: 1) O₃/O₂, 2) dimethyl sulfide / 1) CH₃OH, CH₂Cl₂, -78 deg C, 72 s, 2) CH₃OH, CH₂Cl₂, -78 deg C -> 25 deg C; 25 deg C, 5 h

5: 1) n-BuLi, 2) HMPA / 1) THF, hexane, -78 deg C, 10 min; -78 deg C -> 0 deg C, 20 min, 2) THF, -78 deg C, 1.5 h; 25 deg C, 24 h

With N,N,N,N,N,N-hexamethylphosphoric triamide; N-Bromosuccinimide; n-butyllithium; dimethylsulfide; sulfuric acid; diphenyl phosphoryl azide; oxygen; sodium hydride; ozone; triethylamine; In tetrahydrofuran;

DOI:10.1021/jo9605298

upstream raw materials:

Triphenyl<(2-tetrahydropyranyloxy)methyl>phosphonium chloride

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

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

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

Downstream raw materials:

5-Benzyloxy-3-(tert-butyloxycarbonyl)-8-cyano-1-[(tetrahydropyranyloxy)methyl]-1,2-dihydro-3H-benz[e]indole

(+)-(1R)-5-benzyloxy-3-tert-butoxycarbonyl-1-chloromethyl-8-cyano-1,2-dihydro-3H-benz[e]indole

(-)-(1S)-5-benzyloxy-3-tert-butoxycarbonyl-1-chloromethyl-8-cyano-1,2-dihydro-3H-benz[e]indole

rac-5-benzyloxy-3-tert-butoxycarbonyl-1-chloromethyl-8-cyano-1,2-dihydro-3H-benz[e]indole