tert-butyl trans-4-(cyanofuro[2,3-b]pyridine-2-carbonylamino)cyclohexyloxyacetate

Base Information

Chemical Name:tert-butyl trans-4-(cyanofuro[2,3-b]pyridine-2-carbonylamino)cyclohexyloxyacetate
CAS No.:174775-47-4
Molecular Formula:C₂₁H₂₅N₃O₅
Molecular Weight:399.447
Hs Code.:

Synonyms:tert-butyl trans-4-(cyanofuro[2,3-b]pyridine-2-carbonylamino)cyclohexyloxyacetate

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Chemical Property of tert-butyl trans-4-(cyanofuro[2,3-b]pyridine-2-carbonylamino)cyclohexyloxyacetate

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Technology Process of tert-butyl trans-4-(cyanofuro[2,3-b]pyridine-2-carbonylamino)cyclohexyloxyacetate

There total 7 articles about tert-butyl trans-4-(cyanofuro[2,3-b]pyridine-2-carbonylamino)cyclohexyloxyacetate 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: 46.0%

: 174775-52-1
5-cyanofuro[2,3-b]pyridine-2-carboxylic acid

: 160132-94-5
tert-butyl trans-(4-aminocyclohexyloxy)acetate

: 174775-47-4
tert-butyl trans-4-(cyanofuro[2,3-b]pyridine-2-carbonylamino)cyclohexyloxyacetate

Guidance literature:: With benzotriazol-1-ol; In N,N-dimethyl-formamide; at 20 ℃; for 18h;
DOI:10.1248/cpb.47.1694

Reference yield:

: 6563-64-0
ethyl 5-nitrofuro[2,3-b]pyridine-2-carboxylate

: 174775-47-4
tert-butyl trans-4-(cyanofuro[2,3-b]pyridine-2-carbonylamino)cyclohexyloxyacetate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 96 percent / H₂ / 10 percent Pd/C / ethanol / 15 h / 20 °C

2.1: 12N aq. HCl; NaNO₂ / tetrahydrofuran / 0.33 h / 2 - 3 °C

2.2: 20 percent / KCN / 3.5 h / 3 - 50 °C

3.1: aq. LiOH / tetrahydrofuran / 1 h / 20 °C

4.1: 46 percent / HOBt; EDI / dimethylformamide / 18 h / 20 °C

With hydrogenchloride; lithium hydroxide; hydrogen; benzotriazol-1-ol; sodium nitrite; palladium on activated charcoal; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide; 1.1: Reduction / 2.1: Diazotization / 2.2: Sandmeyer reaction / 3.1: Hydrolysis / 4.1: coupling;
DOI:10.1248/cpb.47.1694

Reference yield:

: 5292-43-3
bromoacetic acid tert-butyl ester

: 174775-47-4
tert-butyl trans-4-(cyanofuro[2,3-b]pyridine-2-carbonylamino)cyclohexyloxyacetate

Guidance literature:: Multi-step reaction with 3 steps

1: 45 percent / n-Bu₄NHSO₄; aq. NaOH / toluene / 15 h / 20 °C

2: 57 percent / aq. NH₄Cl / 2-methyl-propan-2-ol / 2 h / Heating

3: 46 percent / HOBt; EDI / dimethylformamide / 18 h / 20 °C

With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate; ammonium chloride; benzotriazol-1-ol; In N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 1: Substitution / 2: deprotection / 3: coupling;
DOI:10.1248/cpb.47.1694