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

Base Information

• Chemical Name: (2R,6R)-6-Amino-5-oxo-2-(2-thienyl)perhydro-1,4-thiazepine
• CAS No.: 110221-27-7
• Molecular Formula: C9H12N2OS2
• Molecular Weight: 228.33
• DSSTox Substance ID: DTXSID60551265
• Nikkaji Number: J1.629.916B
• Wikidata: Q82430825
• Mol file: 110221-27-7.mol

Synonyms:110221-27-7;(2R,6R)-6-AMINO-5-OXO-2-(2-THIENYL)PERHYDRO-1,4-THIAZEPINE;(2R,6R)-6-amino-2-thiophen-2-yl-1,4-thiazepan-5-one;1,4-Thiazepin-5(2H)-one,6-aminotetrahydro-2-(2-thienyl)-, (2R-cis)- (9CI);DTXSID60551265;(2R,6R)-6-Amino-2-(thiophen-2-yl)-1,4-thiazepan-5-one

Chemical Property of (2R,6R)-6-Amino-5-oxo-2-(2-thienyl)perhydro-1,4-thiazepine

Chemical Property:

• Melting Point: 117-119 °C
• Refractive Index: 1.605
• Boiling Point: 492.768 °C at 760 mmHg
• PKA: 14?+-.0.60(Predicted)
• Flash Point: 251.817 °C
• PSA: 108.66000
• Density: 1.287 g/cm³
• LogP: 2.00860
• 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

(2R,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

Technology Process of (2R,6R)-6-Amino-5-oxo-2-(2-thienyl)perhydro-1,4-thiazepine

There total 4 articles about (2R,6R)-6-Amino-5-oxo-2-(2-thienyl)perhydro-1,4-thiazepine 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:

1-(2-thienyl)-2-nitroethene (34312-77-1) → (2R,6R)-6-amino-2-thienylperhydrothiazepin-5-one (110221-27-7)

Guidance literature:

Multi-step reaction with 4 steps

1: N-methylmorpholine / toluene / 16 h / Ambient temperature

2: 64 percent / H₂, AcOH / 5percent Pd/C / 5 h / 70 °C / 2280 Torr

3: 69 percent / diphenyl phosphorazidate, N-methylmorpholine / dimethylformamide / 16 h / Ambient temperature

4: 31 percent / 4 N aq. HCl / dioxane / 4 h / Ambient temperature

With 4-methyl-morpholine; hydrogenchloride; diphenyl phosphoryl azide; hydrogen; acetic acid; palladium on activated charcoal; In 1,4-dioxane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jm00394a009

Reference yield:

N-t-butoxycarbonyl-S-[2-nitro-1-(thien-2-yl)ethyl]-L-cysteine (102090-86-8) → (2R,6R)-6-amino-2-thienylperhydrothiazepin-5-one (110221-27-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 64 percent / H₂, AcOH / 5percent Pd/C / 5 h / 70 °C / 2280 Torr

2: 69 percent / diphenyl phosphorazidate, N-methylmorpholine / dimethylformamide / 16 h / Ambient temperature

3: 31 percent / 4 N aq. HCl / dioxane / 4 h / Ambient temperature

With 4-methyl-morpholine; hydrogenchloride; diphenyl phosphoryl azide; hydrogen; acetic acid; palladium on activated charcoal; In 1,4-dioxane; N,N-dimethyl-formamide;

DOI:10.1021/jm00394a009

upstream raw materials:

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

1-(2-thienyl)-2-nitroethene

S-[2-amino-1-(thien-2-yl)ethyl]-N-t-butoxycarbonyl-L-cysteine

N-t-butoxycarbonyl-S-[2-nitro-1-(thien-2-yl)ethyl]-L-cysteine

Downstream raw materials:

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

[(2R,6R)-5-Oxo-2-thiophen-2-yl-6-(trityl-amino)-[1,4]thiazepan-4-yl]-acetic acid tert-butyl ester

[(2S,6R)-5-Oxo-2-thiophen-2-yl-6-(trityl-amino)-[1,4]thiazepan-4-yl]-acetic acid tert-butyl ester

[(R)-5-Oxo-2-thiophen-2-yl-6-(trityl-amino)-6,7-dihydro-5H-[1,4]thiazepin-4-yl]-acetic acid tert-butyl ester

Refernces