2-[[[3,5-bis(benzyloxycarbonyl)phenyl]amino]carbonyl]-1,2,3,4,5,6,7,8-octahydro-3-benzazecine

Base Information

• Chemical Name: 2-[[[3,5-bis(benzyloxycarbonyl)phenyl]amino]carbonyl]-1,2,3,4,5,6,7,8-octahydro-3-benzazecine
• CAS No.: 494847-58-4
• Molecular Formula: C₃₆H₃₆N₂O₅
• Molecular Weight: 576.692
• Mol file: 494847-58-4.mol

Synonyms:2-[[[3,5-bis(benzyloxycarbonyl)phenyl]amino]carbonyl]-1,2,3,4,5,6,7,8-octahydro-3-benzazecine

Chemical Property of 2-[[[3,5-bis(benzyloxycarbonyl)phenyl]amino]carbonyl]-1,2,3,4,5,6,7,8-octahydro-3-benzazecine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[[[3,5-bis(benzyloxycarbonyl)phenyl]amino]carbonyl]-1,2,3,4,5,6,7,8-octahydro-3-benzazecine

There total 10 articles about 2-[[[3,5-bis(benzyloxycarbonyl)phenyl]amino]carbonyl]-1,2,3,4,5,6,7,8-octahydro-3-benzazecine 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: 98.0%

2-[[[3,5-bis(benzyloxycarbonyl)phenyl]amino]carbonyl]-N-(tert-butoxycarbonyl)-1,2,3,4,5,6,7,8-octahydro-3-benzazecine (494847-57-3) → 2-[[[3,5-bis(benzyloxycarbonyl)phenyl]amino]carbonyl]-1,2,3,4,5,6,7,8-octahydro-3-benzazecine (494847-58-4)

Guidance literature:

With trifluoroacetic acid; at 20 ℃; for 1h;

DOI:10.1016/S0223-5234(02)01351-X

Reference yield:

5-(2-iodo-phenyl)-pentanal → 2-[[[3,5-bis(benzyloxycarbonyl)phenyl]amino]carbonyl]-1,2,3,4,5,6,7,8-octahydro-3-benzazecine (494847-58-4)

Guidance literature:

Multi-step reaction with 10 steps

1: TsCl; Et₃N

2: 69 percent / NaHCO₃; Bu₄NCl / Pd(OAc)2

3: H₂

4: HCl

5: 63 percent / Et₃N / H₂O; dioxane / 48 h / 20 °C

6: 58 percent / diisopropylethylamine; bromotris(pyrrolidine)phosphonium hexafluorophosphate; DMAP / CH₂Cl₂ / 23 h / 20 °C

7: 98 percent / trifluoroacetic acid / 1 h / 20 °C

With hydrogenchloride; dmap; tetrabutyl-ammonium chloride; hydrogen; sodium hydrogencarbonate; triethylamine; N-ethyl-N,N-diisopropylamine; p-toluenesulfonyl chloride; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; trifluoroacetic acid; palladium diacetate; In 1,4-dioxane; dichloromethane; water; 5: Heck cyclization;

DOI:10.1016/S0223-5234(02)01351-X

Reference yield:

3-Hydroxy-2-[5-(2-iodo-phenyl)-pent-(E)-ylideneamino]-propionic acid methyl ester → 2-[[[3,5-bis(benzyloxycarbonyl)phenyl]amino]carbonyl]-1,2,3,4,5,6,7,8-octahydro-3-benzazecine (494847-58-4)

Guidance literature:

Multi-step reaction with 9 steps

1: TsCl; Et₃N

2: 69 percent / NaHCO₃; Bu₄NCl / Pd(OAc)2

3: H₂

4: HCl

5: 63 percent / Et₃N / H₂O; dioxane / 48 h / 20 °C

6: 58 percent / diisopropylethylamine; bromotris(pyrrolidine)phosphonium hexafluorophosphate; DMAP / CH₂Cl₂ / 23 h / 20 °C

7: 98 percent / trifluoroacetic acid / 1 h / 20 °C

With hydrogenchloride; dmap; tetrabutyl-ammonium chloride; hydrogen; sodium hydrogencarbonate; triethylamine; N-ethyl-N,N-diisopropylamine; p-toluenesulfonyl chloride; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; trifluoroacetic acid; palladium diacetate; In 1,4-dioxane; dichloromethane; water; 4: Heck cyclization;

DOI:10.1016/S0223-5234(02)01351-X

upstream raw materials:

2-[[[3,5-bis(benzyloxycarbonyl)phenyl]amino]carbonyl]-N-(tert-butoxycarbonyl)-1,2,3,4,5,6,7,8-octahydro-3-benzazecine

N-(tert-butoxycarbonyl)-1,2,3,4,5,6,7,8-octahydro-3-benzazecine-2-carboxylic acid

2-{tert-butoxycarbonyl-[5-(2-iodo-phenyl)-pentyl]-amino}-acrylic acid methyl ester

Downstream raw materials:

5-[[[[3,5-bis(benzyloxycarbonyl)phenyl]amino]carbonyl]-[2-(1,2,3,4,5,6,7,8-octahydro-3-benzazecino)carbonyl]]-6-(carboxylic acid)benzimidasole

5-[(3-{6-[(adamantan-1-ylmethyl)-carbamoyl]-3H-benzoimidazole-5-carbonyl}-1,2,3,4,5,6,7,8-octahydro-benzo[d]azecine-2-carbonyl)-amino]-isophthalic acid dibenzyl ester