6-(Mercaptomethyl)-5-oxo-1-thia-4-azacyclotridecane-3-carboxylic acid

Base Information

• Chemical Name: 6-(Mercaptomethyl)-5-oxo-1-thia-4-azacyclotridecane-3-carboxylic acid
• CAS No.: 150198-30-4
• Molecular Formula: C₁₃H₂₃NO₃S₂
• Molecular Weight: 305.463
• DSSTox Substance ID: DTXSID00933889
• Wikidata: Q82909716
• Mol file: 150198-30-4.mol

Synonyms:6-(mercaptomethyl)-5-oxo-1-thia-4-azacyclotridecane-3-carboxylic acid;6-(mercaptomethyl)-5-oxo-1-thia-4-azacyclotridecane-3-carboxylic acid, (3R-(3R*,6R*))-isomer;6-SMOTATCA

Chemical Property of 6-(Mercaptomethyl)-5-oxo-1-thia-4-azacyclotridecane-3-carboxylic acid

Chemical Property:

• Vapor Pressure: 1.05E-14mmHg at 25°C
• Boiling Point: 574.7°Cat760mmHg
• Flash Point: 301.4°C
• PSA: 133.99000
• Density: 1.131g/cm³
• LogP: 2.46510
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 305.11193594
• Heavy Atom Count: 19
• Complexity: 300

Purity/Quality:

6-(MERCAPTOMETHYL)-5-OXO-1-THIA-4-AZACYCLOTRIDECANE-3-CARBOXYLIC ACID 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCCC(C(=O)NC(CSCCC1)C(=O)O)CS
• Isomeric SMILES: C1CCC[C@@H](C(=O)N[C@@H](CSCCC1)C(=O)O)CS

Technology Process of 6-(Mercaptomethyl)-5-oxo-1-thia-4-azacyclotridecane-3-carboxylic acid

There total 21 articles about 6-(Mercaptomethyl)-5-oxo-1-thia-4-azacyclotridecane-3-carboxylic 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: 100.0%

methyl (3R,6S)-6-<(acetylthio)methyl>-5-oxo-1-thia-4-azacyclotridecane-3-carboxylate (150127-15-4) → (3R,6S)-6-(mercaptomethyl)-5-oxo-1-thia-4-azacyclotridecane-3-carboxylic acid (150198-30-4)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; water; for 3h; Ambient temperature;

DOI:10.1021/jm00076a010

Reference yield: 93.0%

methyl (3R,6R)-6-<(acethylthio)methyl>-5-oxo-1-thia-4-azacyclotridecane-3-carboxylate (150198-31-5) → (3R,6R)-6-(mercaptomethyl)-5-oxo-1-thia-4-azacyclotridecane-3-carboxylic acid (150198-30-4)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; water; for 3h; Ambient temperature;

DOI:10.1021/jm00076a010

Reference yield:

1,7-dibromoheptane (4549-31-9) → (3R,6R)-6-(mercaptomethyl)-5-oxo-1-thia-4-azacyclotridecane-3-carboxylic acid (150198-30-4)

Guidance literature:

Multi-step reaction with 10 steps

1: 1.) NaH / 1.) DMF, 0 deg C, 2.) DMF, RT, 3 h

2: 92 percent / NaI / acetone / 2 h / Heating

3: 49 percent / NaOMe / methanol / Ambient temperature

4: 100 percent / HCl (gas) / CH₂Cl₂ / 2 h / Ambient temperature

5: 41 percent / Et₃N, pentafluorophenol, N-<3-(dimethylamino)propyl>-N'-ethylcarbodiimide hydrochloride / CH₂Cl₂ / Ambient temperature

6: 96 percent / 1N aq. NaOH / methanol / 4 h / Ambient temperature

7: 83 percent / piperidine, pyridine / 2 h / 65 °C

8: 86 percent / Ambient temperature

9: 43 percent / methanol; diethyl ether

10: 93 percent / LiOH*H₂O / tetrahydrofuran; H₂O / 3 h / Ambient temperature

With piperidine; pyridine; hydrogenchloride; lithium hydroxide; sodium hydroxide; 2,3,4,5,6-pentafluorophenol; sodium methylate; sodium hydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; sodium iodide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetone;

DOI:10.1021/jm00076a010

upstream raw materials:

methyl (3R,6R)-6-<(acethylthio)methyl>-5-oxo-1-thia-4-azacyclotridecane-3-carboxylate

1,7-dibromoheptane

tert-butyl methyl (7-bromoheptyl)malonate

tert-butyl methyl (7-iodoheptyl)malonate