(S)-3-((tert-butoxycarbonyl)amino)-5-(methylthio)pentanoic acid

Base Information

• Chemical Name: (S)-3-((tert-butoxycarbonyl)amino)-5-(methylthio)pentanoic acid
• CAS No.: 244251-20-5
• Molecular Formula: C11H21NO4S
• Molecular Weight: 263.35
• Hs Code.: 2930909090
• DSSTox Substance ID: DTXSID90947298
• Wikidata: Q82925066
• Mol file: 244251-20-5.mol

Synonyms:1217811-51-2;(S)-3-((tert-butoxycarbonyl)amino)-5-(methylthio)pentanoic acid;(3S)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-5-methylsulfanylpentanoic acid;Pentanoic acid, 3-[[(1,1-dimethylethoxy)carbonyl]amino]-5-(methylthio)-, (3S)-;C11H21NO4S;DTXSID90947298;HBFKPNZCUUZRLA-MRVPVSSYSA-N;MFCD06202399;AKOS015900663;DS-9877;AC-22084;CS-0060982;C71812;EN300-366796;(S)-3-((tert-butoxycarbonyl)amino)-5-(methylthio)pentanoicacid;(3S)-3-{[(tert-butoxy)carbonyl]amino}-5-(methylsulfanyl)pentanoic acid;3-{[tert-Butoxy(hydroxy)methylidene]amino}-5-(methylsulfanyl)pentanoic acid

Chemical Property of (S)-3-((tert-butoxycarbonyl)amino)-5-(methylthio)pentanoic acid

Chemical Property:

• Vapor Pressure: 2.59E-08mmHg at 25°C
• Refractive Index: 1.498
• Boiling Point: 422.3 °C at 760 mmHg
• PKA: 4.36±0.10(Predicted)
• Flash Point: 209.2 °C
• PSA: 100.93000
• Density: 1.137 g/cm³
• LogP: 2.49840
• Storage Temp.: 2-8°C
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 263.11912932
• Heavy Atom Count: 17
• Complexity: 263

Purity/Quality:

97% ^*data from raw suppliers

Boc-L-beta-homomethionine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of (S)-3-((tert-butoxycarbonyl)amino)-5-(methylthio)pentanoic acid

There total 3 articles about (S)-3-((tert-butoxycarbonyl)amino)-5-(methylthio)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: 83.0%

tert-butyl N-{(1S)-3-diazo-1-[2-(methylsulfanyl)ethyl]-2-oxopropyl}carbamate (173472-42-9) → (S)-3-{[(tert-butoxy)carbonyl]amino}-5-(methylsulfanyl)pentanoic acid (244251-20-5,1217811-51-2)

Guidance literature:

With silver trifluoroacetate; triethylamine; In tetrahydrofuran; water; at -25 - 20 ℃; for 3h;

DOI:10.1002/1522-2675(20011017)84:10<2924::AID-HLCA2924>3.0.CO;2-E

Reference yield:

N-tert-butoxycarbonyl-L-methionine (2488-15-5) → (S)-3-{[(tert-butoxy)carbonyl]amino}-5-(methylsulfanyl)pentanoic acid (244251-20-5,1217811-51-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Et₃N; ClCO₂Et / tetrahydrofuran / 0.25 h / -15 - 0 °C

1.2: 71 percent / diethyl ether; tetrahydrofuran / 3 h / 0 - 20 °C

2.1: 83 percent / Et₃N; CF₃CO₂Ag / tetrahydrofuran; H₂O / 3 h / -25 - 20 °C

With silver trifluoroacetate; chloroformic acid ethyl ester; triethylamine; In tetrahydrofuran; water; 2.1: Wolff rearrangement;

DOI:10.1002/1522-2675(20011017)84:10<2924::AID-HLCA2924>3.0.CO;2-E

Reference yield:

diazomethane (186581-53-3,908094-01-9,334-88-3) + N-tert-butoxycarbonyl-L-methionine (2488-15-5) → (S)-3-{[(tert-butoxy)carbonyl]amino}-5-(methylsulfanyl)pentanoic acid (244251-20-5,1217811-51-2)

Guidance literature:

N-tert-butoxycarbonyl-L-methionine; With triethylamine; In tetrahydrofuran; for 0.25h; Inert atmosphere; Cooling with ice;

With chloroformic acid ethyl ester; In tetrahydrofuran; for 0.25h; Inert atmosphere; Cooling with ice;

diazomethane; Further stages;

DOI:10.15227/orgsyn.079.0154

upstream raw materials:

tert-butyl N-{(1S)-3-diazo-1-[2-(methylsulfanyl)ethyl]-2-oxopropyl}carbamate

N-tert-butoxycarbonyl-L-methionine

diazomethane

Downstream raw materials:

Boc-β³-HMet-β³-HMet-β³-HMet-OC6F5