Pentanoic acid, 4-[[(1,1-dimethylethoxy)carbonyl]amino]-, (4S)- (9CI)

Base Information

• Chemical Name: Pentanoic acid, 4-[[(1,1-dimethylethoxy)carbonyl]amino]-, (4S)- (9CI)
• CAS No.: 207924-92-3
• Molecular Formula: C10H19NO4
• Molecular Weight: 217.265
• Hs Code.: 29225090
• Mol file: 207924-92-3.mol

Synonyms:Pentanoic acid, 4-[[(1,1-dimethylethoxy)carbonyl]amino]-, (4S)- (9CI);(S)-4-((tert-Butoxycarbonyl)aMino)pentanoic acid

Chemical Property of Pentanoic acid, 4-[[(1,1-dimethylethoxy)carbonyl]amino]-, (4S)- (9CI)

Chemical Property:

• Melting Point: 75-78 °C
• Boiling Point: 363.2±25.0 °C(Predicted)
• PKA: 4?+-.0.10(Predicted)
• PSA: 75.63000
• Density: 1.081±0.06 g/cm3(Predicted)
• LogP: 2.15530
• Storage Temp.: 2-8°C

Purity/Quality:

98.5% ^*data from raw suppliers

(S)-Boc-4-amino-pentanoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Pentanoic acid, 4-[[(1,1-dimethylethoxy)carbonyl]amino]-, (4S)- (9CI)

There total 9 articles about Pentanoic acid, 4-[[(1,1-dimethylethoxy)carbonyl]amino]-, (4S)- (9CI) 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%

[L-(trans)]-4-[(t-butoxycarbonyl)amino]-2-pentenoic acid (142723-69-1,299182-03-9) → (4S)-4-[(tert-butoxycarbonyl)amino]pentanoic acid (207924-92-3)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; for 3h; under 2327.17 Torr;

DOI:10.1139/v00-066

Reference yield: 100.0%

(E)-(S)-4-tert-Butoxycarbonylamino-pent-2-enoic acid (299182-03-9) → (4S)-4-[(tert-butoxycarbonyl)amino]pentanoic acid (207924-92-3)

Guidance literature:

With palladium on carbon; hydrogen; In ethanol; for 2h; Inert atmosphere;

DOI:10.1002/cmdc.201700370

Reference yield: 69.0%

tert-butyl (1S)-1-methyl-4-diazo-3-oxobutylcarbamate (207924-86-5) → (4S)-4-[(tert-butoxycarbonyl)amino]pentanoic acid (207924-92-3)

Guidance literature:

With silver trifluoroacetate; triethylamine; In tetrahydrofuran; water; at -25 - 20 ℃;

DOI:10.1002/hlca.19980810514

upstream raw materials:

(S)-4-tert-Butoxycarbonylamino-pentanoic acid methyl ester

tert-butyl (1S)-1-methyl-4-diazo-3-oxobutylcarbamate

[L-(trans)]-4-[(t-butoxycarbonyl)amino]-2-pentenoic acid

(S)-N-(tert-butoxycarbonyl)alanine methyl ester

Downstream raw materials:

(S)-4-Aminovaleric acid

(R)-4-((S)-4-tert-Butoxycarbonylamino-pentanoylamino)-6-methyl-heptanoic acid benzyl ester

(R)-4-[(S)-4-((R)-4-{(R)-4-[(S)-4-((R)-4-tert-Butoxycarbonylamino-5-methyl-hexanoylamino)-pentanoylamino]-6-methyl-heptanoylamino}-5-methyl-hexanoylamino)-pentanoylamino]-6-methyl-heptanoic acid benzyl ester

(R)-4-[(S)-4-((R)-4-tert-Butoxycarbonylamino-5-methyl-hexanoylamino)-pentanoylamino]-6-methyl-heptanoic acid benzyl ester

Refernces

• 1、 Benke, Sushil N.,Thulasiram, Hirekodathakallu V.,Gopi, Hosahudya N.. "Potent Antimicrobial Activity of Lipidated Short α,γ-Hybrid Peptides". supporting information. p. 1610 - 1615. Retrieved 2017/10/16.
• 2、 Yang, Hua,Jurkauskas, Valdas,Mackintosh, Nicole,Mogren, Tobias,Stephenson, Corey R. J.,Foster, Katherine,Brown, William,Roberts, Edward. "Trifluoroacetic acid-mediated intramolecular formal N-H insertion reactions with amino-α-diazoketones: A facile and efficient synthesis of optically pure pyrrolidinones and piperidinones". . p. 800 - 808. Retrieved 2007/10/03.