5-[(E)-2-(Benzyloxycarbamoyl-methyl)-3-phenyl-acryloylamino]-pentanoic acid tert-butyl ester

Base Information

Chemical Name:5-[(E)-2-(Benzyloxycarbamoyl-methyl)-3-phenyl-acryloylamino]-pentanoic acid tert-butyl ester
CAS No.:120686-45-5
Molecular Formula:C₂₇H₃₄N₂O₅
Molecular Weight:466.577
Hs Code.:

Synonyms:5-[(E)-2-(Benzyloxycarbamoyl-methyl)-3-phenyl-acryloylamino]-pentanoic acid tert-butyl ester

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Chemical Property of 5-[(E)-2-(Benzyloxycarbamoyl-methyl)-3-phenyl-acryloylamino]-pentanoic acid tert-butyl ester

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Technology Process of 5-[(E)-2-(Benzyloxycarbamoyl-methyl)-3-phenyl-acryloylamino]-pentanoic acid tert-butyl ester

There total 5 articles about 5-[(E)-2-(Benzyloxycarbamoyl-methyl)-3-phenyl-acryloylamino]-pentanoic acid tert-butyl ester 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: 55.3%

: 2687-43-6
O-benzylhydoxylamine hydrochloride

: 120686-36-4
5-((E)-2-Carboxymethyl-3-phenyl-acryloylamino)-pentanoic acid tert-butyl ester

: 120686-45-5
5-[(E)-2-(Benzyloxycarbamoyl-methyl)-3-phenyl-acryloylamino]-pentanoic acid tert-butyl ester

Guidance literature:: With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; chloroform; 1.) 0 deg C, 1 h, 2.) r.t., overnight;
DOI:10.1021/jm00127a017

Reference yield:

: 63983-88-0
tert-butyl 5-{[(benzyloxy)carbonyl]amino}pentanoate

: 120686-45-5
5-[(E)-2-(Benzyloxycarbamoyl-methyl)-3-phenyl-acryloylamino]-pentanoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: hydrogen / 10 percent Pd/charcoal / methanol / 5 h / Ambient temperature

2: 98.7 percent / 1-hydroxybenzotriazole, N,N'-dicyclohexylcarbodiimide / tetrahydrofuran; CHCl₃ / 1.) 0 deg C, 1 h, 2.) r.t., overnight

3: 58.1 percent / 1 M NaOH / ethanol; H₂O / 1.) 0 deg C, 1 h, 2.) r.t., 5 h

4: 55.3 percent / triethylamine, 1-hydroxybenzotriazole, N,N'-dicyclohexylcarbodiimide / tetrahydrofuran; CHCl₃ / 1.) 0 deg C, 1 h, 2.) r.t., overnight

With sodium hydroxide; hydrogen; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; chloroform; water;
DOI:10.1021/jm00127a017

Reference yield:

: 23135-50-4
5-(N-benzyloxycarbonylamino)pentanoic acid

: 120686-45-5
5-[(E)-2-(Benzyloxycarbamoyl-methyl)-3-phenyl-acryloylamino]-pentanoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: benzene / 0.5 h / Heating

2: hydrogen / 10 percent Pd/charcoal / methanol / 5 h / Ambient temperature

3: 98.7 percent / 1-hydroxybenzotriazole, N,N'-dicyclohexylcarbodiimide / tetrahydrofuran; CHCl₃ / 1.) 0 deg C, 1 h, 2.) r.t., overnight

4: 58.1 percent / 1 M NaOH / ethanol; H₂O / 1.) 0 deg C, 1 h, 2.) r.t., 5 h

5: 55.3 percent / triethylamine, 1-hydroxybenzotriazole, N,N'-dicyclohexylcarbodiimide / tetrahydrofuran; CHCl₃ / 1.) 0 deg C, 1 h, 2.) r.t., overnight

With sodium hydroxide; hydrogen; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; chloroform; water; benzene;
DOI:10.1021/jm00127a017