(S)-2-((tert-Butoxycarbonyl)amino)-5-(dimethylamino)-5-oxopentanoic acid

Base Information

• Chemical Name: (S)-2-((tert-Butoxycarbonyl)amino)-5-(dimethylamino)-5-oxopentanoic acid
• CAS No.: 72449-42-4
• Molecular Formula: C₁₂H₂₂N₂O₅
• Molecular Weight: 274.317
• European Community (EC) Number: 878-738-5
• Nikkaji Number: J1.752.549B
• Mol file: 72449-42-4.mol

Synonyms:72449-42-4;(S)-2-((tert-Butoxycarbonyl)amino)-5-(dimethylamino)-5-oxopentanoic acid;(2S)-5-(dimethylamino)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxopentanoic acid;C12H22N2O5;N2-[(1,1-Dimethylethoxy)carbonyl]-N,N-dimethyl-L-glutamine;(2S)-2-{[(tert-butoxy)carbonyl]amino}-4-(dimethylcarbamoyl)butanoic acid;Boc-Glu(NMe2)-OH;SCHEMBL13914082;XCA44942;MFCD29920880;AKOS027335639;CS-W000726;AS-48513;F50329;EN300-7367601;N2-(tert-Butoxycarbonyl)-N5,N5-dimethyl-L-glutamine;(S)-2-(Boc-amino)-5-(dimethylamino)-5-oxopentanoic Acid;L-Glutamine, N2-[(1,1-dimethylethoxy)carbonyl]-N,N-dimethyl-;(2S)-2-[(tert-butoxycarbonyl)amino]-4-(dimethylcarbamoyl)butanoic acid;(S)-2-((t-Butoxycarbonyl)amino)-5-(dimethylamino)-5-oxopentanoic acid;(S)-2-((tert-Butoxycarbonyl)amino)-5-(dimethylamino)-5-oxopentanoicacid

Chemical Property of (S)-2-((tert-Butoxycarbonyl)amino)-5-(dimethylamino)-5-oxopentanoic acid

Chemical Property:

• Boiling Point: 460.4±40.0 °C(Predicted)
• PKA: 3.84±0.10(Predicted)
• Density: 1.150±0.06 g/cm3(Predicted)
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 274.15287181
• Heavy Atom Count: 19
• Complexity: 347

Purity/Quality:

99% ^*data from raw suppliers

(S)-2-((tert-Butoxycarbonyl)amino)-5-(dimethylamino)-5-oxopentanoicacid 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CCC(=O)N(C)C)C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CCC(=O)N(C)C)C(=O)O

Technology Process of (S)-2-((tert-Butoxycarbonyl)amino)-5-(dimethylamino)-5-oxopentanoic acid

There total 2 articles about (S)-2-((tert-Butoxycarbonyl)amino)-5-(dimethylamino)-5-oxopentanoic acid 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: 90.0%

N2-(tert-butyloxycarbonyl)-N5,N5-dimethylglutamine benzyl ester (72468-46-3) → Boc-Gln(Me2)-OH (72449-42-4)

Guidance literature:

With hydrogen; 10percent Pd/C; In methanol; for 6h;

DOI:10.1021/jo0157831

Reference yield:

Boc-Glu-OBn (30924-93-7) → Boc-Gln(Me2)-OH (72449-42-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: ClCOOEt; Et₃N / CH₂Cl₂ / 0.08 h / 0 °C

1.2: 85 percent / Et₃N / CH₂Cl₂

2.1: 90 percent / H₂ / 10percent Pd/C / methanol / 6 h

With hydrogen; chloroformic acid ethyl ester; triethylamine; 10percent Pd/C; In methanol; dichloromethane;

DOI:10.1021/jo0157831

Reference yield: 68.0%

4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + Boc-Gln(Me2)-OH (72449-42-4) → N2-(tert-butyloxycarbonyl)-N5,N5-dimethylglutamine p-nitrophenyl ester (72449-43-5)

Guidance literature:

With dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; at 0 - 4 ℃; for 17h;

DOI:10.1021/jm00176a020

upstream raw materials:

N²-(tert-butyloxycarbonyl)-N⁵,N⁵-dimethylglutamine benzyl ester

Boc-Glu-OBn

Downstream raw materials:

N²-(tert-butyloxycarbonyl)-N⁵,N⁵-dimethylglutamine p-nitrophenyl ester

Boc-Gln(Me₂)-D-Trp(CHO)-Phe-NMeBzl

[(S)-1-((4R,7S,13S,16S,19R)-13,16-Dibenzyl-4-carbamoyl-7-isobutyl-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaaza-cycloicos-19-ylcarbamoyl)-3-dimethylcarbamoyl-propyl]-carbamic acid tert-butyl ester

(S)-4-tert-Butoxycarbonylamino-6-dimethylcarbamoyl-2-fluoro-3-oxo-hexanoic acid benzyl ester

Refernces

• 1、 Stahl, Glenn L.,Smith, Clark W.,Walter, Roderich,Tsegenidis, theodor,Stavropoulos, George,et al.. "Oxytocin and Lysine-vasopressin with N5,N5-Dialkylglutamine in the 4 Position: Effect of Introducing Sterically Hindered Groups into the Hydrophilic Cluster of Neurohypophyseal Hormones". . p. 213 - 217. Retrieved 2007/10/02.