4-[4-[(2S)-2-Oxiranylmethoxy]-1,2,5-thiadiazol-3-YL]-morpholine

Base Information

• Chemical Name: 4-[4-[(2S)-2-Oxiranylmethoxy]-1,2,5-thiadiazol-3-YL]-morpholine
• CAS No.: 69500-53-4
• Molecular Formula: C9H13N3O3S
• Molecular Weight: 243.287
• DSSTox Substance ID: DTXSID80458782
• Nikkaji Number: J2.072.932E
• Wikidata: Q82282302
• Mol file: 69500-53-4.mol

Synonyms:69500-53-4;4-[4-[(2S)-2-OXIRANYLMETHOXY]-1,2,5-THIADIAZOL-3-YL]-MORPHOLINE;(S)-4-[4-(OXIRANYLMETHOXY)-1,2,5-THIADIAZOL-3-YL]MORPHOLINE;4-[4-[[(2S)-oxiran-2-yl]methoxy]-1,2,5-thiadiazol-3-yl]morpholine;(S)-4-(4-(Oxiran-2-ylmethoxy)-1,2,5-thiadiazol-3-yl)morpholine;4-(4-{[(2S)-oxiran-2-yl]methoxy}-1,2,5-thiadiazol-3-yl)morpholine;starbld0006372;SCHEMBL10338456;DTXSID80458782;ZGZYFNICRHUUGD-ZETCQYMHSA-N;AKOS030242674;AG-G-70630;3-Morpholino-4-[[(S)-oxiranyl]methoxy]-1,2,5-thiadiazole

Chemical Property of 4-[4-[(2S)-2-Oxiranylmethoxy]-1,2,5-thiadiazol-3-YL]-morpholine

Chemical Property:

• Vapor Pressure: 5.8E-07mmHg at 25°C
• Boiling Point: 410.9°C at 760 mmHg
• Flash Point: 202.3°C
• PSA: 88.25000
• Density: 1.406g/cm³
• LogP: 0.21730
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 243.06776246
• Heavy Atom Count: 16
• Complexity: 240

Purity/Quality:

97% ^*data from raw suppliers

(S)-4-[4-(Oxiranylmethoxy)-1,2,5-thiadiazol-3-yl]morpholine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1COCCN1C2=NSN=C2OCC3CO3
• Isomeric SMILES: C1COCCN1C2=NSN=C2OC[C@@H]3CO3
• Uses: (S)-4-[4-(Oxiranylmethoxy)-1,2,5-thiadiazol-3-yl]morpholine (cas# 69500-53-4) is a compound useful in organic synthesis.

Technology Process of 4-[4-[(2S)-2-Oxiranylmethoxy]-1,2,5-thiadiazol-3-YL]-morpholine

There total 11 articles about 4-[4-[(2S)-2-Oxiranylmethoxy]-1,2,5-thiadiazol-3-YL]-morpholine 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: 97.0%

(2R)-1-chloro-3-[(4-morpholin-4-yl-1,2,5-thiadiazol-3-yl)oxy]propan-2-ol (935528-00-0) → 4-{4-[(2S)-oxiran-2-ylmethoxy]-1,2,5-thiadiazol-3-yl}morpholine (69500-53-4)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; at 0 - 25 ℃; for 1h;

DOI:10.1016/j.tet.2007.01.057

Reference yield: 45.0%

4-{4-[(2R/S)-oxiran-2-ylmethoxy]-1,2,5-thiadiazol-3-yl}morpholine (58827-68-2) → (R)-3-(4-morpholin-4-yl-[1,2,5]thiadiazol-3-yloxy)-propane-1,2-diol + 4-{4-[(2S)-oxiran-2-ylmethoxy]-1,2,5-thiadiazol-3-yl}morpholine (69500-53-4) + 4-{4-[(2R)-oxiran-2-ylmethoxy]-1,2,5-thiadiazol-3-yl}morpholine (741719-53-9)

Guidance literature:

With acetic acid; (S,S)-salen-cobalt(II); In tetrahydrofuran; water; at 0 - 20 ℃; for 8h; Title compound not separated from byproducts;

DOI:10.1016/j.tet.2007.01.057

Reference yield:

3-hydroxy-4-(N-morpholino)-1,2,5-thiadiazole (30165-97-0) → 4-{4-[(2S)-oxiran-2-ylmethoxy]-1,2,5-thiadiazol-3-yl}morpholine (69500-53-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / potassium tert-butoxide / tetrahydrofuran / 5 h / 25 °C

2: acetic acid / (S,S)-salen-cobalt(II) / tetrahydrofuran; H₂O / 8 h / 0 - 20 °C

With potassium tert-butylate; acetic acid; (S,S)-salen-cobalt(II); In tetrahydrofuran; water;

DOI:10.1016/j.tet.2007.01.057

upstream raw materials:

tert-butyl-[(S)-2-hydroxy-3-(4-morpholin-4-yl-[1,2,5]thiadiazol-3-yloxy)-propyl]-dimethyl-ammonium; iodide

3-Morpholino-4-chloro-1,2,5-thiadiazole

(R)-oxiranemethanol

3-hydroxy-4-(N-morpholino)-1,2,5-thiadiazole

Downstream raw materials:

timolol maleate

timolol

Refernces

• 1、 Kong, Xu-Dong,Ma, Qian,Zhou, Jiahai,Zeng, Bu-Bing,Xu, Jian-He. "A smart library of epoxide hydrolase variants and the top hits for synthesis of (S)-β-blocker precursors". supporting information. p. 6641 - 6644. Retrieved 2014/07/08.
• 2、 Tosi, Giovanni,Zironi, Federica,Caselli, Emilia,Forni, Arrigo,Prati, Fabio. "Biocatalytic asymmetric synthesis of (S)- and (R)-Timolol". . p. 1625 - 1628. Retrieved 2007/10/03.