(S)-3-tert-Butylcarbamoyl-4-((2S,4R)-4-carboxy-2-hydroxy-5-phenyl-pentyl)-piperazine-1-carboxylic acid tert-butyl ester

Base Information

Chemical Name:(S)-3-tert-Butylcarbamoyl-4-((2S,4R)-4-carboxy-2-hydroxy-5-phenyl-pentyl)-piperazine-1-carboxylic acid tert-butyl ester
CAS No.:1027528-21-7
Molecular Formula:C₂₆H₄₁N₃O₆
Molecular Weight:491.628
Hs Code.:

Synonyms:(S)-3-tert-Butylcarbamoyl-4-((2S,4R)-4-carboxy-2-hydroxy-5-phenyl-pentyl)-piperazine-1-carboxylic acid tert-butyl ester

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Chemical Property of (S)-3-tert-Butylcarbamoyl-4-((2S,4R)-4-carboxy-2-hydroxy-5-phenyl-pentyl)-piperazine-1-carboxylic acid tert-butyl ester

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Technology Process of (S)-3-tert-Butylcarbamoyl-4-((2S,4R)-4-carboxy-2-hydroxy-5-phenyl-pentyl)-piperazine-1-carboxylic acid tert-butyl ester

There total 11 articles about (S)-3-tert-Butylcarbamoyl-4-((2S,4R)-4-carboxy-2-hydroxy-5-phenyl-pentyl)-piperazine-1-carboxylic 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:

: 32780-06-6
(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran

: 1027528-21-7
(S)-3-tert-Butylcarbamoyl-4-((2S,4R)-4-carboxy-2-hydroxy-5-phenyl-pentyl)-piperazine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 96 percent / imidazole / CH₂Cl₂ / 4 h / 0 - 20 °C

2: 1.) LDA / 1.) THF, hexane, 30 min, 2.) THF, hexane, 3 h

3: 97 percent / 49percent aq. HF / acetonitrile / 18 h / Ambient temperature

4: 96 percent / 2,6-lutidine / CH₂Cl₂ / 1.5 h / 0 °C

5: 83 percent / (i-Pr)2NEt / propan-2-ol / 3.5 h

6: aq. LiOH / 1,2-dimethoxy-ethane / 0.5 h

With 1H-imidazole; 2,6-dimethylpyridine; lithium hydroxide; hydrogen fluoride; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In 1,2-dimethoxyethane; dichloromethane; isopropyl alcohol; acetonitrile;
DOI:10.1021/jm00047a001

Reference yield:

: 58632-95-4
2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile

: 1027528-21-7
(S)-3-tert-Butylcarbamoyl-4-((2S,4R)-4-carboxy-2-hydroxy-5-phenyl-pentyl)-piperazine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 40percent NaOH / dioxane; H₂O / 2.5 h

2: 40percent NaOH / dioxane; H₂O / 14 h

3: 85 percent / 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride, HOBt, Et₃N / dimethylformamide / 18 h

4: 96 percent / H₂ / 10percent Pd/C / methanol / 3 h

5: 83 percent / (i-Pr)2NEt / propan-2-ol / 3.5 h

6: aq. LiOH / 1,2-dimethoxy-ethane / 0.5 h

With lithium hydroxide; sodium hydroxide; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In 1,4-dioxane; methanol; 1,2-dimethoxyethane; water; N,N-dimethyl-formamide; isopropyl alcohol;
DOI:10.1021/jm00047a001

Reference yield:

: 848482-93-9
(S)-4-(tert-butoxycarbonyl)piperazine-2-carboxylic acid

: 1027528-21-7
(S)-3-tert-Butylcarbamoyl-4-((2S,4R)-4-carboxy-2-hydroxy-5-phenyl-pentyl)-piperazine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 40percent NaOH / dioxane; H₂O / 14 h

2: 85 percent / 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride, HOBt, Et₃N / dimethylformamide / 18 h

3: 96 percent / H₂ / 10percent Pd/C / methanol / 3 h

4: 83 percent / (i-Pr)2NEt / propan-2-ol / 3.5 h

5: aq. LiOH / 1,2-dimethoxy-ethane / 0.5 h

With lithium hydroxide; sodium hydroxide; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In 1,4-dioxane; methanol; 1,2-dimethoxyethane; water; N,N-dimethyl-formamide; isopropyl alcohol;
DOI:10.1021/jm00047a001