tert-butyl (2S)-5-amino-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoate

Base Information

• Chemical Name: tert-butyl (2S)-5-amino-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoate
• CAS No.: 53054-03-8
• Molecular Formula: C₁₄H₂₈N₂O₄
• Molecular Weight: 288.387
• Mol file: 53054-03-8.mol

Synonyms:tert-butyl (2S)-5-amino-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoate

Chemical Property of tert-butyl (2S)-5-amino-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoate

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

N2-Boc-L-ornithinetert-butylester 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of tert-butyl (2S)-5-amino-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoate

There total 9 articles about tert-butyl (2S)-5-amino-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoate 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: 98.0%

Nα-(1,1-dimethylethoxycarbonyl)-Nδ-(phenylmethoxycarbonyl)-L-ornithine 1,1-dimethylethyl ester (53054-02-7) → tert-butyl (2S)-5-amino-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoate (53054-03-8)

Guidance literature:

With hydrogen; palladium on activated charcoal; under 760 Torr;

DOI:10.1021/jo00068a031

Reference yield:

Boc-Orn(Z)-OH (2480-93-5) → tert-butyl (2S)-5-amino-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoate (53054-03-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / 4-(dimethylamino)pyridine / 2-methyl-propan-2-ol / 2 h

2: H₂ / Pd/C / methanol

With dmap; hydrogen; palladium on activated charcoal; In methanol; tert-butyl alcohol;

DOI:10.1016/j.bmc.2005.12.043

Reference yield:

(S)-2-amino-5-(((benzyloxy)carbonyl)amino)pentanoic acid tert-butyl ester (53054-01-6) → tert-butyl (2S)-5-amino-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoate (53054-03-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / Et₃N / dioxane; H₂O / 5 h

2: 77 percent / H₂ / Pd/C / ethanol / 48 h

With hydrogen; triethylamine; palladium on activated charcoal; In 1,4-dioxane; ethanol; water; 1: Acylation / 2: Hydrogenolysis;

DOI:10.1016/S0968-0896(99)00136-4

upstream raw materials:

N_α-(1,1-dimethylethoxycarbonyl)-N_δ-(phenylmethoxycarbonyl)-L-ornithine 1,1-dimethylethyl ester

N₂-(tert-butoxycarbonyl)-L-ornithine

tert-butyl alcohol

Boc-Orn(Z)-OH

Downstream raw materials:

C₂₆H₄₁FN₄O₆

C₂₆H₄₈N₄O₆

N_α-(1,1-dimethylethoxycarbonyl)-N_δ-aminothiocarbonylornithine 1,1-dimethylethyl ester

2-tert-butoxycarbonylamino-5-{[3-(N'-isobutyryl-hydrazinocarbonyl)-4-methoxy-phenylaminooxalyl]-amino}-pentanoic acid tert-butyl ester