(R)-2-[(Formyl-hydroxy-amino)-methyl]-N-((S)-1-hydroxy-2-oxo-azepan-3-yl)-3-phenyl-propionamide

Base Information

Chemical Name:(R)-2-[(Formyl-hydroxy-amino)-methyl]-N-((S)-1-hydroxy-2-oxo-azepan-3-yl)-3-phenyl-propionamide
CAS No.:440679-71-0
Molecular Formula:C₁₇H₂₃N₃O₅
Molecular Weight:349.387
Hs Code.:

Synonyms:(R)-2-[(Formyl-hydroxy-amino)-methyl]-N-((S)-1-hydroxy-2-oxo-azepan-3-yl)-3-phenyl-propionamide

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (R)-2-[(Formyl-hydroxy-amino)-methyl]-N-((S)-1-hydroxy-2-oxo-azepan-3-yl)-3-phenyl-propionamide

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Technology Process of (R)-2-[(Formyl-hydroxy-amino)-methyl]-N-((S)-1-hydroxy-2-oxo-azepan-3-yl)-3-phenyl-propionamide

There total 11 articles about (R)-2-[(Formyl-hydroxy-amino)-methyl]-N-((S)-1-hydroxy-2-oxo-azepan-3-yl)-3-phenyl-propionamide 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: 96.0%

: 440679-76-5
(R)-2-[(Benzyloxy-formyl-amino)-methyl]-N-((S)-1-hydroxy-2-oxo-azepan-3-yl)-3-phenyl-propionamide

: 440679-71-0
(R)-2-[(Formyl-hydroxy-amino)-methyl]-N-((S)-1-hydroxy-2-oxo-azepan-3-yl)-3-phenyl-propionamide

Guidance literature:: With hydrogen; palladium on activated charcoal; In methanol; at 20 ℃; for 3h;
DOI:10.1021/ol025896m

Reference yield:

: 2212-75-1
N₂-[(benzyloxy)carbonyl]-L-lysine

: 440679-71-0
(R)-2-[(Formyl-hydroxy-amino)-methyl]-N-((S)-1-hydroxy-2-oxo-azepan-3-yl)-3-phenyl-propionamide

Guidance literature:: Multi-step reaction with 8 steps

1.1: KOH / methanol / 16 h / 20 °C

2.1: m-CPBA / methanol / 2 h / 0 °C

2.2: TFA / CH₂Cl₂ / 1 h / 20 °C

2.3: 66 percent / ethyl acetate / 0 - 20 °C

3.1: NH₂OH*HCl / methanol / 0.33 h / 65 °C

4.1: 55 percent / EDC; HOAt; NaHCO₃ / acetonitrile; dimethylformamide / 48 h / 20 °C

5.1: H₂ / Pd/C / methanol / 1 h / 20 °C

6.1: 33 percent / EDC; HOAt; DMAP / dimethylformamide / 48 h / 20 °C

7.1: 90 percent / tetrahydrofuran / 16 h / 0 °C

8.1: 96 percent / H₂ / Pd/C / methanol / 3 h / 20 °C

With dmap; potassium hydroxide; 1-hydroxy-7-aza-benzotriazole; hydroxylamine hydrochloride; hydrogen; sodium hydrogencarbonate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/ol025896m

Reference yield:

: 123802-80-2
(R)-2-hydroxymethyl-3-phenylpropionic acid

: 440679-71-0
(R)-2-[(Formyl-hydroxy-amino)-methyl]-N-((S)-1-hydroxy-2-oxo-azepan-3-yl)-3-phenyl-propionamide

Guidance literature:: Multi-step reaction with 6 steps

1: 80 percent / EDC; DMAP / H₂O; dimethylformamide / 16 h / 20 °C

2: 83 percent / PPh₃; CCl₄; Et₃N / acetonitrile / 12 h / 20 °C

3: aq. HCl / dioxane / 1 h / 60 °C

4: 33 percent / EDC; HOAt; DMAP / dimethylformamide / 48 h / 20 °C

5: 90 percent / tetrahydrofuran / 16 h / 0 °C

6: 96 percent / H₂ / Pd/C / methanol / 3 h / 20 °C

With hydrogenchloride; tetrachloromethane; dmap; 1-hydroxy-7-aza-benzotriazole; hydrogen; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/ol025896m