(S)-1-tert-Butyl 5-methyl 2-((tert-butoxycarbonyl)amino)pentanedioate

Base Information

• Chemical Name: (S)-1-tert-Butyl 5-methyl 2-((tert-butoxycarbonyl)amino)pentanedioate
• CAS No.: 24277-38-1
• Molecular Formula: C15H27NO6
• Molecular Weight: 317.382
• Mol file: 24277-38-1.mol

Synonyms:α-tert-butyl γ-methyl N-Boc-L-glutamate;(S)-(-)-1-tert-butyl-5-methyl-[(2-tert-butoxycarbonyl)amino]pentanedioate;Boc-Glu(OMe)-OtBu;1-tert-butyl 5-methyl (2S)-2-{[(tert-butoxy)carbonyl]amino}pentanedioate;α-tert-butyl γ-methyl N-(tert-butoxycarbonyl)-L-glutamate;

Chemical Property of (S)-1-tert-Butyl 5-methyl 2-((tert-butoxycarbonyl)amino)pentanedioate

Chemical Property:

• Melting Point: 65-67 °C(Solv: ethanol, 50% (64-17-5))
• Boiling Point: 403.1±35.0 °C(Predicted)
• PKA: 10.86±0.46(Predicted)
• PSA: 90.93000
• Density: 1.072±0.06 g/cm3(Predicted)
• LogP: 2.56550
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform, DCM

Purity/Quality:

98% ^*data from raw suppliers

N-Boc 1-O-t-Butyl 5-O-Methoxy L-Glutamic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: N-Boc 1-O-t-Butyl 5-O-Methoxy L-Glutamic Acid is an intermediate used in the synthesis of Isodesmosine Chloride Hydrate (Synthetic) (I815051), which is a component of elastin and also it is extremely hygroscopic and must be stored over a desiccant such as silica gel.

Technology Process of (S)-1-tert-Butyl 5-methyl 2-((tert-butoxycarbonyl)amino)pentanedioate

There total 1 articles about (S)-1-tert-Butyl 5-methyl 2-((tert-butoxycarbonyl)amino)pentanedioate 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: 50.0%

tert-butyl (S)-N-tert-butoxycarbonylpyroglutamate (91229-91-3) + methyl chloroformate (79-22-1) → (S)-(-)-1-tert-butyl-5-methyl-<(2-tert-butoxycarbonyl)amino>pentanedioate (24277-38-1)

Guidance literature:

tert-butyl (S)-N-tert-butoxycarbonylpyroglutamate; With lithium hydroxide; In tetrahydrofuran; at 0 ℃;

methyl chloroformate; With dmap; triethylamine; In dichloromethane; at 0 ℃; Further stages.;

DOI:10.1016/j.tetlet.2004.02.118

Reference yield: 84.0%

(S)-(-)-1-tert-butyl-5-methyl-<(2-tert-butoxycarbonyl)amino>pentanedioate (24277-38-1) → N-tert-butoxycarbonyl glutamic acid tert-butyl ester (24277-39-2)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; water;

DOI:10.1016/j.bmcl.2006.12.056

Reference yield: 81.0%

benzyl bromide (100-39-0) + (S)-(-)-1-tert-butyl-5-methyl-<(2-tert-butoxycarbonyl)amino>pentanedioate (24277-38-1) → 2-benzyl-4-tert-butoxycarbonylamino-pentanedioic acid 5-tert-butyl ester 1-methyl ester (528588-35-4)

Guidance literature:

(S)-(-)-1-tert-butyl-5-methyl-<(2-tert-butoxycarbonyl)amino>pentanedioate; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.5h;

benzyl bromide; In tetrahydrofuran;

DOI:10.1016/S0040-4039(02)02865-4

upstream raw materials:

tert-butyl (S)-N-tert-butoxycarbonylpyroglutamate

methyl chloroformate

Downstream raw materials:

N-tert-butoxycarbonyl glutamic acid tert-butyl ester

2-benzyl-4-tert-butoxycarbonylamino-pentanedioic acid 5-tert-butyl ester 1-methyl ester

1-tert-butyl 5-methyl (2S,4S)-4-[(4-bromophenyl)methyl]-2-{[(tert-butoxy)carbonyl]amino}pentanedioate

Boc-Glu

Refernces