(S)-2-(N-tert-butoxycarbonyl-N'-allyloxycarbonylhydrazinomethyl)-2,5-dihydropyrrole-1-carboxylic acid benzyl ester

Base Information

• Chemical Name: (S)-2-(N-tert-butoxycarbonyl-N'-allyloxycarbonylhydrazinomethyl)-2,5-dihydropyrrole-1-carboxylic acid benzyl ester
• CAS No.: 648934-32-1
• Molecular Formula: C₂₂H₂₉N₃O₆
• Molecular Weight: 431.489
• Mol file: 648934-32-1.mol

Synonyms:(S)-2-(N-tert-butoxycarbonyl-N'-allyloxycarbonylhydrazinomethyl)-2,5-dihydropyrrole-1-carboxylic acid benzyl ester

Chemical Property of (S)-2-(N-tert-butoxycarbonyl-N'-allyloxycarbonylhydrazinomethyl)-2,5-dihydropyrrole-1-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-(N-tert-butoxycarbonyl-N'-allyloxycarbonylhydrazinomethyl)-2,5-dihydropyrrole-1-carboxylic acid benzyl ester

There total 5 articles about (S)-2-(N-tert-butoxycarbonyl-N'-allyloxycarbonylhydrazinomethyl)-2,5-dihydropyrrole-1-carboxylic acid benzyl 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: 79.0%

di-tert-butyl dicarbonate (24424-99-5) + (S)-2-(N'-allyloxycarbonylhydrazinomethyl)-2,5-dihydropyrrole-1-carboxylic acid benzyl ester (648934-27-4) → (S)-2-(N-tert-butoxycarbonyl-N'-allyloxycarbonylhydrazinomethyl)-2,5-dihydropyrrole-1-carboxylic acid benzyl ester (648934-32-1)

Guidance literature:

With triethylamine; In methanol; at 60 ℃;

DOI:10.1016/j.bmcl.2005.01.022

Reference yield:

(2S)-2,5-dihydro-1H-pyrrole-1,2-dicarboxylic acid 2-methyl 1-(phenylmethyl) ester (5211-24-5) → (S)-2-(N-tert-butoxycarbonyl-N'-allyloxycarbonylhydrazinomethyl)-2,5-dihydropyrrole-1-carboxylic acid benzyl ester (648934-32-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 90 percent / LiBH₄ / methanol; tetrahydrofuran

2: Et₃N / CH₂Cl₂

3: sodium azide / dimethylformamide / 110 °C

4: 74 percent / PPh₃; H₂O / dioxane / 50 °C

5: 36 percent / CH₂Cl₂

6: 79 percent / Et₃N / methanol / 60 °C

With lithium borohydride; sodium azide; water; triethylamine; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2005.01.022

Reference yield:

(S)-2-aminomethyl-2,5-dihydropyrrole-1-carboxylic acid benzyl ester (648934-24-1) → (S)-2-(N-tert-butoxycarbonyl-N'-allyloxycarbonylhydrazinomethyl)-2,5-dihydropyrrole-1-carboxylic acid benzyl ester (648934-32-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 36 percent / CH₂Cl₂

2: 79 percent / Et₃N / methanol / 60 °C

With triethylamine; In methanol; dichloromethane;

DOI:10.1016/j.bmcl.2005.01.022

upstream raw materials:

di-tert-butyl dicarbonate

(S)-2-(N'-allyloxycarbonylhydrazinomethyl)-2,5-dihydropyrrole-1-carboxylic acid benzyl ester

(2S)-2,5-dihydro-1H-pyrrole-1,2-dicarboxylic acid 2-methyl 1-(phenylmethyl) ester

(S)-2-aminomethyl-2,5-dihydropyrrole-1-carboxylic acid benzyl ester

Downstream raw materials:

(3aR,6S,6aS)-1-[(2S)-2-(4-tert-butylbenzoylamino)-4-methylpentanoyl]-6-hydroxyhexahydropyrrolo[3,2-c]pyrazole-2,4-dicarboxylic acid 4-benzyl ester 2-tert-butyl ester

(3aR,6S,6aS)-4-benzoyl-1-[(2S)-2-(4-tert-butylbenzoylamino)-4-methylpentanoyl]-6-hydroxyhexahydropyrrolo[3,2-c]pyrazole-2-carboxylic acid tert-butyl ester

(3aR,6aS)-4-benzoyl-1-[(2S)-2-(4-tert-butylbenzoylamino)-4-methylpentanoyl]-6-oxo-hexahydropyrrolo[3,2-c]pyrazole-2-carboxylic acid tert-butyl ester

(2S)-2-{N-tert-butoxycarbonyl-N'-[(2S)-2-(4-tert-butylbenzoylamino)-4-methylpentanoyl]-hydrazinomethyl}-2,5-dihydropyrrole-1-carboxylic acid benzyl ester