1-(4,5-Dihydrothiazol-2-yl)azetidin-3-ol

Base Information

• Chemical Name: 1-(4,5-Dihydrothiazol-2-yl)azetidin-3-ol
• CAS No.: 161715-27-1
• Molecular Formula: C6H10N2OS
• Molecular Weight: 158.224
• Hs Code.: 2934100090
• DSSTox Substance ID: DTXSID60450764
• Wikidata: Q72481963
• Mol file: 161715-27-1.mol

Synonyms:1-(4,5-Dihydrothiazol-2-yl)azetidin-3-ol;161715-27-1;1-(4,5-dihydro-1,3-thiazol-2-yl)azetidin-3-ol;3-hydroxy-1-(1,3-thiazolin-2-yl)azetidine;SCHEMBL6600380;DTXSID60450764;SBRPTNRHTKKATC-UHFFFAOYSA-N;SB67393;3-hydroxy-1-(thiazolin-2-yl)azetidine;FT-0740648;A883065

Chemical Property of 1-(4,5-Dihydrothiazol-2-yl)azetidin-3-ol

Chemical Property:

• Melting Point: 114-117℃
• Boiling Point: 306.812 °C at 760 mmHg
• PKA: 13.70±0.20(Predicted)
• Flash Point: 139.355 °C
• PSA: 61.13000
• Density: 1.595 g/cm³
• LogP: -0.86080
• Storage Temp.: 2-8°C
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 158.05138412
• Heavy Atom Count: 10
• Complexity: 165

Purity/Quality:

99.50% ^*data from raw suppliers

1-(4,5-Dihydrothiazol-2-yl)azetidin-3-ol 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CSC(=N1)N2CC(C2)O

Technology Process of 1-(4,5-Dihydrothiazol-2-yl)azetidin-3-ol

There total 1 articles about 1-(4,5-Dihydrothiazol-2-yl)azetidin-3-ol 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: 92.0%

2-methylsulfanyl-4,5-dihydrothiazoline (19975-56-5) + azetion-3-ol hydrochloride (18621-18-6) → 1-(1,3-thiazolin-2-yl-)azetidin-3-ol (161715-27-1)

Guidance literature:

With potassium hydrogencarbonate; In methanol; for 23h; Heating;

DOI:10.1038/ja.2006.34

Reference yield:

1-(1,3-thiazolin-2-yl-)azetidin-3-ol (161715-27-1) → (+)-(4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-3-{[1-(2-thiazolin-2-yl)-3-azetidinyl]sulfanyl}-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid-p-nitrobenzyl ester (161715-20-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 93 percent / DMAP; Et₃N / tetrahydrofuran / 0.5 h / 5 °C

2.1: 88 percent / potassium thioacetate / dimethylformamide / 5.5 h / 100 °C

3.1: KOH / propan-2-ol; methanol / 0.17 h / 5 °C

3.2: 87 percent / HCl / propan-2-ol; methanol / 15 h / 5 °C

4.1: 94 percent / diisopropyl ethylamine; MeCN / 2 h / -20 °C

With dmap; potassium hydroxide; triethylamine; N-ethyl-N,N-diisopropylamine; acetonitrile; potassium thioacetate; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; isopropyl alcohol;

DOI:10.1038/ja.2006.34

Reference yield:

1-(1,3-thiazolin-2-yl-)azetidin-3-ol (161715-27-1) → Tebipenem (161715-21-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 93 percent / DMAP; Et₃N / tetrahydrofuran / 0.5 h / 5 °C

2.1: 88 percent / potassium thioacetate / dimethylformamide / 5.5 h / 100 °C

3.1: KOH / propan-2-ol; methanol / 0.17 h / 5 °C

3.2: 87 percent / HCl / propan-2-ol; methanol / 15 h / 5 °C

4.1: 94 percent / diisopropyl ethylamine; MeCN / 2 h / -20 °C

5.1: 82 percent / sodium hydrogen carbonate / Pd-C / butan-1-ol; H₂O / 1.5 h / 20 °C / 3000.24 Torr

With dmap; potassium hydroxide; sodium hydrogencarbonate; triethylamine; N-ethyl-N,N-diisopropylamine; acetonitrile; potassium thioacetate; palladium on activated charcoal; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide; isopropyl alcohol; butan-1-ol;

DOI:10.1038/ja.2006.34

upstream raw materials:

2-methylsulfanyl-4,5-dihydrothiazoline

azetion-3-ol hydrochloride

Downstream raw materials:

Tebipenem

3-acetylthio-1-(1,3-thiazolin-2-yl)azetidine

(+)-(4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-3-{[1-(2-thiazolin-2-yl)-3-azetidinyl]sulfanyl}-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid-p-nitrobenzyl ester

tebipenem