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

Base Information

Chemical Name:(R)-2-[(Benzyloxy-formyl-amino)-methyl]-N-((S)-1-hydroxy-2-oxo-azepan-3-yl)-3-phenyl-propionamide
CAS No.:440679-76-5
Molecular Formula:C₂₄H₂₉N₃O₅
Molecular Weight:439.511
Hs Code.:

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

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

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

There total 11 articles about (R)-2-[(Benzyloxy-formyl-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: 90.0%

: 3197-61-3
N-formylimidazole

: 440679-75-4
(R)-2-(Benzyloxyamino-methyl)-N-((S)-1-hydroxy-2-oxo-azepan-3-yl)-3-phenyl-propionamide

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

Guidance literature:: In tetrahydrofuran; at 0 ℃; for 16h;
DOI:10.1021/ol025896m

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 7 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

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:

: 171287-56-2
(S)-2-Benzyloxycarbonylamino-6-hydroxyamino-hexanoic acid

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

Guidance literature:: Multi-step reaction with 4 steps

1: 55 percent / EDC; HOAt; NaHCO₃ / acetonitrile; dimethylformamide / 48 h / 20 °C

2: H₂ / Pd/C / methanol / 1 h / 20 °C

3: 33 percent / EDC; HOAt; DMAP / dimethylformamide / 48 h / 20 °C

4: 90 percent / tetrahydrofuran / 16 h / 0 °C

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