(2S,6R)-6-amino-2-(2-thienyl)-1,4-thiazepan-5-one

Base Information

• Chemical Name: (2S,6R)-6-amino-2-(2-thienyl)-1,4-thiazepan-5-one
• CAS No.: 110221-26-6
• Molecular Formula: C9H12N2OS2
• Molecular Weight: 228.34
• DSSTox Substance ID: DTXSID00551264
• Nikkaji Number: J1.629.925A
• Wikidata: Q72442563
• Mol file: 110221-26-6.mol

Synonyms:110221-26-6;(2S,6R)-6-amino-2-(2-thienyl)-1,4-thiazepan-5-one;(2S,6R)-6-amino-2-(thiophen-2-yl)-1,4-thiazepan-5-one;(2S,6R)-6-Amino-5-oxo-2-(2-thienyl)perhydro-1,4-thiazepine;(2S,6R)-6-amino-2-thiophen-2-yl-1,4-thiazepan-5-one;C9H12N2OS2;DTXSID00551264;BCP14797;MFCD08458730;SC3641;AKOS015918385;AC-4304;AS-15998;CS-0053401;(+)-6-Amino-2-(2-thienyl)-1,4-thiazepan-5-one;J-002403;(2S,6R)-6-amino-2-(thiophen-2-yl)-1a,4-thiazepan-5-one

Chemical Property of (2S,6R)-6-amino-2-(2-thienyl)-1,4-thiazepan-5-one

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 7.46E-10mmHg at 25°C
• Melting Point: 163-1650 °C
• Refractive Index: 1.604
• Boiling Point: 492.8 °C at 760 mmHg
• PKA: 14?+-.0.60(Predicted)
• Flash Point: 251.8 °C
• PSA: 108.66000
• Density: 1.286 g/cm³
• LogP: 2.00860
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility.: DMF (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 228.03910536
• Heavy Atom Count: 14
• Complexity: 225

Purity/Quality:

99% ^*data from raw suppliers

(2S,6R)-6-Amino-5-oxo-2-(2-thienyl)perhydro-1,4-thiazepine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(SCC(C(=O)N1)N)C2=CC=CS2
• Isomeric SMILES: C1[C@H](SC[C@@H](C(=O)N1)N)C2=CC=CS2
• Uses: Temocapril intermediate

Technology Process of (2S,6R)-6-amino-2-(2-thienyl)-1,4-thiazepan-5-one

There total 1 articles about (2S,6R)-6-amino-2-(2-thienyl)-1,4-thiazepan-5-one 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: 35.0%

6(R)-t-butoxycarbonylamino-5-oxo-2-(2-thienyl)perhydro-1,4-thiazepine (950913-92-5) → (2R,6R)-6-amino-2-thienylperhydrothiazepin-5-one (110221-27-7) + (2S,6R)-6-Amino-2-thiophen-2-yl-[1,4]thiazepan-5-one (110221-26-6)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; for 4h; Ambient temperature;

DOI:10.1021/jm00394a009

Reference yield: 80.0%

ethyl (R)-4-phenyl-2-<<(trifluoromethyl)sulfonyl>oxy>butyrate (88767-98-0,138333-09-2) + (2S,6R)-6-Amino-2-thiophen-2-yl-[1,4]thiazepan-5-one (110221-26-6) → (S)-2-((2S,6R)-5-Oxo-2-thiophen-2-yl-[1,4]thiazepan-6-ylamino)-4-phenyl-butyric acid ethyl ester (110143-57-2)

Guidance literature:

With triethylamine; In dichloromethane; for 16h; Ambient temperature;

DOI:10.1021/jm00394a009

Reference yield:

(2S,6R)-6-Amino-2-thiophen-2-yl-[1,4]thiazepan-5-one (110221-26-6) → (S)-2-((2S,6R)-4-tert-Butoxycarbonylmethyl-5-oxo-2-thiophen-2-yl-[1,4]thiazepan-6-ylamino)-4-phenyl-butyric acid ethyl ester (110221-37-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / Et₃N / CH₂Cl₂ / 16 h / Ambient temperature

2: 94 percent / NaH / dimethylformamide / 5 h / Ambient temperature

With sodium hydride; triethylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00394a009

upstream raw materials:

6(R)-t-butoxycarbonylamino-5-oxo-2-(2-thienyl)perhydro-1,4-thiazepine

Downstream raw materials:

(S)-2-((2S,6R)-5-Oxo-2-thiophen-2-yl-[1,4]thiazepan-6-ylamino)-4-phenyl-butyric acid ethyl ester

(S)-2-((2S,6R)-4-tert-Butoxycarbonylmethyl-5-oxo-2-thiophen-2-yl-[1,4]thiazepan-6-ylamino)-4-phenyl-butyric acid ethyl ester

temocapril Hydrochloride

[3H]-Temocaprilat