2-([(Tert-butoxy)carbonyl]amino)pentanoic acid

Base Information

• Chemical Name: 2-([(Tert-butoxy)carbonyl]amino)pentanoic acid
• CAS No.: 53308-95-5
• Molecular Formula: C10H19NO4
• Molecular Weight: 217.265
• Hs Code.: 29241990
• European Community (EC) Number: 818-447-2
• NSC Number: 343953,186911
• DSSTox Substance ID: DTXSID20307083
• Mol file: 53308-95-5.mol

Synonyms:521286-38-4;rac-Boc Norvaline;2-([(TERT-BUTOXY)CARBONYL]AMINO)PENTANOIC ACID;2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoic acid;2-{[(tert-butoxy)carbonyl]amino}pentanoic acid;2-((tert-Butoxycarbonyl)amino)pentanoic acid;Boc-D-2-aminovaleric acid;2-tert-Butoxycarbonylamino-pentanoic acid;2-(Boc-amino)pentanoic Acid;MFCD00270725;2-[(tert-butoxycarbonyl)amino]pentanoic acid;MFCD00037268;Boc-DL-norvaline;NSC343953;N-Boc-aminovaleric acid;Norvaline,N-[(1,1-dimethylethoxy)carbonyl]-(9CI);SCHEMBL1231627;DTXSID20307083;t-butoxycarbonylamino valeric acid;INWOAUUPYIXDHN-UHFFFAOYSA-N;STR07898;NSC186911;AKOS009157797;NSC-186911;NSC-343953;SY017991;CS-0453253;FT-0640466;FT-0658255;FT-0663546;EN300-62478;D86426;2-([(TERT-BUTOXY)CARBONYL]AMINO)PENTANOICACID;Z444321096

Chemical Property of 2-([(Tert-butoxy)carbonyl]amino)pentanoic acid

Chemical Property:

• Appearance/Colour: transparent solid
• Vapor Pressure: 8.85E-06mmHg at 25°C
• Melting Point: 43-47 °C
• Refractive Index: 1.4500 (estimate)
• Boiling Point: 348.306 °C at 760 mmHg
• PKA: 4.02±0.20(Predicted)
• Flash Point: 164.45 °C
• PSA: 75.63000
• Density: 1.081 g/cm³
• LogP: 2.15530
• Storage Temp.: 0-6°C
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 217.13140809
• Heavy Atom Count: 15
• Complexity: 232

Purity/Quality:

99% ^*data from raw suppliers

Boc-L-norvaline ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCC(C(=O)O)NC(=O)OC(C)(C)C
• Uses: BOC-L-Norvaline is used in the synthesis of α-amino acid ester prodrugs used as cytotoxic agents against human lung cancer.

Technology Process of 2-([(Tert-butoxy)carbonyl]amino)pentanoic acid

There total 12 articles about 2-([(Tert-butoxy)carbonyl]amino)pentanoic 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: 98.0%

D,L-N-Boc-nor-valine methyl ester (142729-70-2) → N-tert-butoxycarbonyl-L-norvaline (53308-95-5) + (R)-2-tert-butoxycarbonylaminopentanoic acid methyl ester (116611-58-6)

Guidance literature:

With Bacillus licheniformis; In water; at 30 ℃; for 15h; pH=7.5;

DOI:10.1016/j.tetasy.2006.07.012

Reference yield: 95.0%

L-Norvaline (6600-40-4,498-18-0) + di-tert-butyl dicarbonate (24424-99-5) → N-tert-butoxycarbonyl-L-norvaline (53308-95-5)

Guidance literature:

L-Norvaline; With sodium hydroxide; In tetrahydrofuran; water; at 0 ℃; for 0.166667h;

di-tert-butyl dicarbonate; In tetrahydrofuran; water; at 0 - 20 ℃; for 24h;

DOI:10.1002/anie.201507321

Reference yield:

tert-butyl [(1S)-1-(hydroxymethyl)butyl]carbamate (116611-57-5,116611-55-3) → N-tert-butoxycarbonyl-L-norvaline (53308-95-5)

Guidance literature:

With dipyridinium dichromate; In N,N-dimethyl-formamide; at 25 ℃; for 6h;

DOI:10.1016/S0040-4039(00)96866-7

upstream raw materials:

L-Norvaline

2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile

tert-butyl [(1S)-1-(hydroxymethyl)butyl]carbamate

di-tert-butyl dicarbonate

Downstream raw materials:

(S)-1-((S)-2-tert-Butoxycarbonylamino-pentanoyl)-pyrrolidine-2-carboxylic acid benzyl ester

(S)-2-tert-Butoxycarbonylamino-pentanoic acid (1S,2S)-2-benzyloxycarbonylamino-1-((R)-4-tert-butylcarbamoyl-thiazolidine-3-carbonyl)-3-phenyl-propyl ester

methyl N-{[(1,1-dimethylethyl)oxy]carbonyl}-L-norvalinate

tert-butyl [(1S)-1-(hydroxymethyl)butyl]carbamate

Refernces

• 1、 Naskar, Jishu,Roy, Subhasish,Joardar, Anindita,Das, Sumantra,Banerjee, Arindam. "Self-assembling dipeptide-based nontoxic vesicles as carriers for drugs and other biologically important molecules". supporting information; experimental part. p. 6610 - 6615. Retrieved 2011/11/07.
• 2、 Catalano, John G,Deaton, David N,Furfine, Eric S,Hassell, Annie M,McFadyen, Robert B,Miller, Aaron B,Miller, Larry R,Shewchuk, Lisa M,Willard Jr., Derril H,Wright, Lois L. "Exploration of the P1 SAR of aldehyde cathepsin K inhibitors.". . p. 275 - 278. Retrieved 2007/10/03.