3,5-bis[(N-benzyloxycarbonyl)aminomethyl]-3',5'-bis[(N-tert-butyloxycarbonyl)aminomethyl]biphenyl

Base Information

• Chemical Name: 3,5-bis[(N-benzyloxycarbonyl)aminomethyl]-3',5'-bis[(N-tert-butyloxycarbonyl)aminomethyl]biphenyl
• CAS No.: 214828-10-1
• Molecular Formula: C₄₂H₅₀N₄O₈
• Molecular Weight: 738.881

Synonyms:3,5-bis[(N-benzyloxycarbonyl)aminomethyl]-3',5'-bis[(N-tert-butyloxycarbonyl)aminomethyl]biphenyl

Chemical Property of 3,5-bis[(N-benzyloxycarbonyl)aminomethyl]-3',5'-bis[(N-tert-butyloxycarbonyl)aminomethyl]biphenyl

Chemical Property:

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Technology Process of 3,5-bis[(N-benzyloxycarbonyl)aminomethyl]-3',5'-bis[(N-tert-butyloxycarbonyl)aminomethyl]biphenyl

There total 6 articles about 3,5-bis[(N-benzyloxycarbonyl)aminomethyl]-3',5'-bis[(N-tert-butyloxycarbonyl)aminomethyl]biphenyl 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: 91.0%

3,5-bis[(N-tert-butoxycarbonyl)aminomethyl]-1-iodobenzene + 3,5-bis[(N-benzyloxycarbonyl)aminomethyl]-1-iodobenzene → 3,5-bis[(N-benzyloxycarbonyl)aminomethyl]-3',5'-bis[(N-tert-butyloxycarbonyl)aminomethyl]biphenyl (214828-10-1)

Guidance literature:

3,5-bis[(N-tert-butoxycarbonyl)aminomethyl]-1-iodobenzene; With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; bis(pinacol)diborane; In N,N-dimethyl-formamide; at 80 ℃; for 6h;

3,5-bis[(N-benzyloxycarbonyl)aminomethyl]-1-iodobenzene; With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; In water; N,N-dimethyl-formamide; at 80 ℃; for 17h;

DOI:10.1002/anie.200461409

Reference yield:

5-bromo-1,3-xylene (556-96-7) → 3,5-bis[(N-benzyloxycarbonyl)aminomethyl]-3',5'-bis[(N-tert-butyloxycarbonyl)aminomethyl]biphenyl (214828-10-1)

Guidance literature:

Multi-step reaction with 5 steps

1: NBS, AIBN / methyl formate / Irradiation

2: dimethylformamide

3: N₂H₄*H₂O / CH₂Cl₂; methanol

4: (i-Pr)2NEt / tetrahydrofuran

5: 1.) (SnBu₃)2, 2.) NMP / 1.) Pd(OAc)2, PPh₃, 2.) Pd₂(dba)3, tri-(2-furyl)phosphane / 1.) toluene, reflux, 2.) 50 deg C

With 1-methyl-pyrrolidin-2-one; N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); bis(tri-n-butyltin); hydrazine hydrate; N-ethyl-N,N-diisopropylamine; palladium diacetate; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; trifuran-2-yl-phosphane; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; Methyl formate; N,N-dimethyl-formamide;

DOI:10.1002/(SICI)1521-3773(19980904)37:16<2270::AID-ANIE2270>3.0.CO;2-6

Reference yield:

1-bromo-3,5-bis(bromomethyl)benzene (51760-23-7) → 3,5-bis[(N-benzyloxycarbonyl)aminomethyl]-3',5'-bis[(N-tert-butyloxycarbonyl)aminomethyl]biphenyl (214828-10-1)

Guidance literature:

Multi-step reaction with 4 steps

1: dimethylformamide

2: N₂H₄*H₂O / CH₂Cl₂; methanol

3: (i-Pr)2NEt / tetrahydrofuran

4: 1.) (SnBu₃)2, 2.) NMP / 1.) Pd(OAc)2, PPh₃, 2.) Pd₂(dba)3, tri-(2-furyl)phosphane / 1.) toluene, reflux, 2.) 50 deg C

With 1-methyl-pyrrolidin-2-one; bis(tri-n-butyltin); hydrazine hydrate; N-ethyl-N,N-diisopropylamine; palladium diacetate; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; trifuran-2-yl-phosphane; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/(SICI)1521-3773(19980904)37:16<2270::AID-ANIE2270>3.0.CO;2-6

upstream raw materials:

5-bromo-1,3-xylene

1-bromo-3,5-bis(bromomethyl)benzene

1,3-bis(aminomethyl)-5-bromobenzene

5-bromo-1,3-bis(phthalimidomethyl)benzene

Downstream raw materials:

3,5-bis(aminomethyl)-3'5'-bis[(N-benzyloxycarbonyl)aminomethyl]biphenyl

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