benzyl N-{(2S,3S)-3-[(tert-butoxycarbonyl)amino]-2-hydroxy-4-phenylbutanoyl}piperidine-4-carboxylate

Base Information

Chemical Name:benzyl N-{(2S,3S)-3-[(tert-butoxycarbonyl)amino]-2-hydroxy-4-phenylbutanoyl}piperidine-4-carboxylate
CAS No.:851968-89-3
Molecular Formula:C₂₈H₃₆N₂O₆
Molecular Weight:496.604
Hs Code.:

Synonyms:benzyl N-{(2S,3S)-3-[(tert-butoxycarbonyl)amino]-2-hydroxy-4-phenylbutanoyl}piperidine-4-carboxylate

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Chemical Property of benzyl N-{(2S,3S)-3-[(tert-butoxycarbonyl)amino]-2-hydroxy-4-phenylbutanoyl}piperidine-4-carboxylate

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Technology Process of benzyl N-{(2S,3S)-3-[(tert-butoxycarbonyl)amino]-2-hydroxy-4-phenylbutanoyl}piperidine-4-carboxylate

There total 1 articles about benzyl N-{(2S,3S)-3-[(tert-butoxycarbonyl)amino]-2-hydroxy-4-phenylbutanoyl}piperidine-4-carboxylate 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: 82.0%

: 62023-65-8,76498-21-0,77171-41-6,82848-28-0,105181-72-4,116661-86-0
(2S,3S)-3-tert-butoxycarbonylamino-2-hydroxy-4-phenylbutanoic acid

: benzyl piperidine-4-carboxylate hydrochloride

: 851968-89-3
benzyl N-{(2S,3S)-3-[(tert-butoxycarbonyl)amino]-2-hydroxy-4-phenylbutanoyl}piperidine-4-carboxylate

Guidance literature:: With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 0 - 20 ℃;
DOI:10.1016/j.tet.2005.01.135

Reference yield:

: 851968-89-3
benzyl N-{(2S,3S)-3-[(tert-butoxycarbonyl)amino]-2-hydroxy-4-phenylbutanoyl}piperidine-4-carboxylate

: 1-((2S,3S)-3-Amino-2-hydroxy-4-phenyl-butyryl)-piperidine-4-carboxylic acid benzyl ester

Guidance literature:: With hydrogenchloride; In 1,4-dioxane; at 0 - 20 ℃;
DOI:10.1016/j.tet.2005.01.135

Reference yield:

: 851968-89-3
benzyl N-{(2S,3S)-3-[(tert-butoxycarbonyl)amino]-2-hydroxy-4-phenylbutanoyl}piperidine-4-carboxylate

: N-{N-[(4S,5R)-4-benzyl-1,3-oxazolidin-2-one-5-carbonyl]piperidine-4-carbonyl}-(R)-1-phenylethylamine

Guidance literature:: Multi-step reaction with 8 steps

1.1: HCl / dioxane / 0 - 20 °C

2.1: 4.0 g / triethylamine / tetrahydrofuran / 0 - 20 °C

3.1: 4.7 g / triethylamine; LiCl / tetrahydrofuran / -18 - 20 °C

4.1: LDA / tetrahydrofuran / 0.5 h / -78 °C

4.2: 86 percent / NH₄Cl / tetrahydrofuran

5.1: LDA / tetrahydrofuran / 0.5 h / -78 °C

5.2: 87 percent / tetrahydrofuran / 3 h / -78 - 0 °C

6.1: LiOH; H₂O₂ / tetrahydrofuran / 0 °C

7.1: H₂ / Pd/C / methanol; H₂O / 3 h

8.1: 133.7 mg / 1-ethyl-3-(3-(dimetyhylamino)propyl)carbodiimide*HCl; HOBt*H₂O; triethylamine / dimethylformamide / 0 - 20 °C

With hydrogenchloride; lithium hydroxide; hydrogen; dihydrogen peroxide; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; lithium chloride; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; water; N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2005.01.135