Boc-Sar-OSu

Base Information

• Chemical Name: Boc-Sar-OSu
• CAS No.: 80621-90-5
• Molecular Formula: C12H18 N2 O6
• Molecular Weight: 286.285
• DSSTox Substance ID: DTXSID40448548
• Nikkaji Number: J1.656.826K
• Mol file: 80621-90-5.mol

Synonyms:Boc-Sar-OSu;80621-90-5;Boc-N-Me-Gly-OSu;(2,5-dioxopyrrolidin-1-yl) 2-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]acetate;2,5-dioxo-1-pyrrolidinyl n-methyl-n-(((2-methyl-2-propanyl)oxy)carbonyl)glycinate;2,5-Dioxo-1-pyrrolidinyl N-methyl-N-{[(2-methyl-2-propanyl)oxy]carbonyl}glycinate;Boc-L-Sar-Osu;Boc-N-methylglycine N-hydroxysuccinimide ester;SCHEMBL4595993;DTXSID40448548;FVEKCHUPMRHPKK-UHFFFAOYSA-N;MFCD00153312;AKOS016001401;Boc-sarcosine N-hydroxysuccinimide ester;BS-29468;CS-0173541;A864675;2,5-dioxopyrrolidin-1-yl N-(tert-butoxycarbonyl)-N-methylglycinate;2,5-dioxopyrrolidin-1-yl 2-(tert-butoxycarbonyl(methyl)amino)acetate;N-(tert-Butyloxycarbonyl)-N-methylglycine 2,5-dioxo-1-pyrrolidinyl ester;Glycine,N-[(1,1-dimethylethoxy)carbonyl]-N-methyl-, 2,5-dioxo-1-pyrrolidinyl ester;N-t-Butyloxycarbonyl-sarcosine succinimidyl ester, N-t-Butyloxycarbonyl-N-methyl-glycine succinimidyl ester

Chemical Property of Boc-Sar-OSu

Chemical Property:

• Boiling Point: 377.9±35.0 °C(Predicted)
• PKA: -1.79±0.70(Predicted)
• PSA: 93.22000
• Density: 1.28±0.1 g/cm3(Predicted)
• LogP: 0.39840
• Storage Temp.: -15°C
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 286.11648630
• Heavy Atom Count: 20
• Complexity: 424

Purity/Quality:

98.5% ^*data from raw suppliers

Boc-N-methylglycine N-hydroxysuccinimide ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N(C)CC(=O)ON1C(=O)CCC1=O

Technology Process of Boc-Sar-OSu

There total 2 articles about Boc-Sar-OSu 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: 100.0%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + N-(tert-butoxycarbonyl)sarcosine (13734-36-6) → tert-butyl N-{2-[(2,5-dioxopyrrolidin-1-yl)oxy]-2-hydroxyethyl}-N-methylcarbamate (80621-90-5)

Guidance literature:

With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 - 20 ℃; for 20h;

Reference yield:

2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile (58632-95-4) → tert-butyl N-{2-[(2,5-dioxopyrrolidin-1-yl)oxy]-2-hydroxyethyl}-N-methylcarbamate (80621-90-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / Et₃N / H₂O; dioxane / 18 h

2: EDC / ethyl acetate; dimethylformamide / 18 h

With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In 1,4-dioxane; water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2004.07.034

Reference yield: 62.0%

tert-butyl N-{2-[(2,5-dioxopyrrolidin-1-yl)oxy]-2-hydroxyethyl}-N-methylcarbamate (80621-90-5) + 1,3,5-cis,cis-triamino-cyclohexane trihydrobromide → ({3,5-bis-[2-(tert-butoxycarbonyl-methyl-amino)-acetylamino]-cyclohexylcarbamoyl}-methyl)-methyl-carbamic acid tert-butyl ester (769950-62-1)

Guidance literature:

cis,cis-1,3,5-triaminocyclohexane trihydrochloride; With sodium hydroxide; at 20 ℃;

tert-butyl N-{2-[(2,5-dioxopyrrolidin-1-yl)oxy]-2-hydroxyethyl}-N-methylcarbamate; In N,N-dimethyl-formamide; benzene; at 45 ℃; for 18h;

DOI:10.1016/j.bmc.2004.07.034

upstream raw materials:

1-hydroxy-pyrrolidine-2,5-dione

N-(tert-butoxycarbonyl)sarcosine

2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile

Downstream raw materials:

Boc-Sar-Lys(Z)-Pro-OMe

Boc-Sar-Sar-Lys(Z)-Pro-OMe

2-[1-[2-(tert-butoxycarbonyl-methyl-amino)-acetylamino]-2-(4-fluoro-phenyl)-ethyl]-thiazole-4-carboxylic acid ethyl ester

({3,5-bis-[2-(tert-butoxycarbonyl-methyl-amino)-acetylamino]-cyclohexylcarbamoyl}-methyl)-methyl-carbamic acid tert-butyl ester

Refernces

• 1、 Harada, Naoya,Kimura, Hiroyuki,Ono, Masahiro,Saji, Hideo. "Preparation of asymmetric urea derivatives that target prostate-specific membrane antigen for SPECT imaging". . p. 7890 - 7901. Retrieved 2013/11/06.
• 2、 Camphausen, Kevin,Sproull, Mary,Tantama, Steve,Venditto, Vincent,Sankineni, Sandeep,Scott, Tamalee,Brechbiel, Martin W.. "Evaluation of chelating agents as anti-angiogenic therapy through copper chelation". . p. 5133 - 5140. Retrieved 2007/10/03.