Ethyl {1-[(benzyloxy)methyl]-1H-tetrazol-5-yl}acetate

Base Information

• Chemical Name: Ethyl {1-[(benzyloxy)methyl]-1H-tetrazol-5-yl}acetate
• CAS No.: 88669-73-2
• Molecular Formula: C13H16N4O3
• DSSTox Substance ID: DTXSID90542489
• Wikidata: Q82419176
• Mol file: 88669-73-2.mol

Synonyms:88669-73-2;Ethyl {1-[(benzyloxy)methyl]-1H-tetrazol-5-yl}acetate;DTXSID90542489

Chemical Property of Ethyl {1-[(benzyloxy)methyl]-1H-tetrazol-5-yl}acetate

Chemical Property:

• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 8
• Exact Mass: 276.12224039
• Heavy Atom Count: 20
• Complexity: 297

Purity/Quality:

85.0-99.8% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)CC1=NN=NN1COCC2=CC=CC=C2

Technology Process of Ethyl {1-[(benzyloxy)methyl]-1H-tetrazol-5-yl}acetate

There total 1 articles about Ethyl {1-[(benzyloxy)methyl]-1H-tetrazol-5-yl}acetate 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:

Benzyloxymethyl chloride (3587-60-8) + ethyl (tetrazol-5-yl)acetate (13616-37-0) → (2-Benzyloxymethyl-2H-tetrazol-5-yl)-acetic acid ethyl ester (88669-78-7) + (1-Benzyloxymethyl-1H-tetrazol-5-yl)-acetic acid ethyl ester (88669-73-2)

Guidance literature:

DOI:10.1021/ja00318a042

Reference yield:

(1-Benzyloxymethyl-1H-tetrazol-5-yl)-acetic acid ethyl ester (88669-73-2) → Trifluoro-methanesulfonic acid (5R,6S)-2-(1-benzyloxymethyl-1H-tetrazol-5-yl)-6-((R)-1-hydroxy-ethyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-3-yl ester (88670-01-3)

Guidance literature:

Multi-step reaction with 6 steps

1: saponification

2: 1.) dibutylmagnesium; 2.) carbonyl diimidazole / 1.) THF, heptane, 0 deg C; 2.) THF

3: HF / H₂O; acetonitrile

4: Et₃N, p-(C₁₂H₂₅)C₆H₄SO₂N₃ / CH₂Cl₂

5: rhodium (II) acetate dimer / CH₂Cl₂ / Heating

6: 1,8-diazabicyclo<5.4.0>undec-7-ene / tetrahydrofuran / -78 °C

With dirhodium tetraacetate; p-(C₁₂H₂₅)C₆H₄SO₂N₃; hydrogen fluoride; dibutylmagnesium; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 1,1'-carbonyldiimidazole; In tetrahydrofuran; dichloromethane; water; acetonitrile;

DOI:10.1021/ja00318a042

Reference yield:

(1-Benzyloxymethyl-1H-tetrazol-5-yl)-acetic acid ethyl ester (88669-73-2) → {2-[(5R,6S)-2-(1-Benzyloxymethyl-1H-tetrazol-5-yl)-6-((R)-1-hydroxy-ethyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-3-ylsulfanyl]-ethyl}-carbamic acid 4-nitro-benzyl ester (88670-00-2)

Guidance literature:

Multi-step reaction with 7 steps

1: saponification

2: 1.) dibutylmagnesium; 2.) carbonyl diimidazole / 1.) THF, heptane, 0 deg C; 2.) THF

3: HF / H₂O; acetonitrile

4: Et₃N, p-(C₁₂H₂₅)C₆H₄SO₂N₃ / CH₂Cl₂

5: rhodium (II) acetate dimer / CH₂Cl₂ / Heating

6: 1,8-diazabicyclo<5.4.0>undec-7-ene / tetrahydrofuran / -78 °C

With dirhodium tetraacetate; p-(C₁₂H₂₅)C₆H₄SO₂N₃; hydrogen fluoride; dibutylmagnesium; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 1,1'-carbonyldiimidazole; In tetrahydrofuran; dichloromethane; water; acetonitrile;

DOI:10.1021/ja00318a042

upstream raw materials:

Benzyloxymethyl chloride

ethyl (tetrazol-5-yl)acetate

Downstream raw materials:

(3S,4R)-4-[3-(1-Benzyloxymethyl-1H-tetrazol-5-yl)-2-oxo-propyl]-3-((R)-1-hydroxy-ethyl)-azetidin-2-one

(2S,5R,6S)-2-(1-Benzyloxymethyl-1H-tetrazol-5-yl)-6-((R)-1-hydroxy-ethyl)-1-aza-bicyclo[3.2.0]heptane-3,7-dione

(5R,6S)-2-(1-Benzyloxymethyl-1H-tetrazol-5-yl)-3-ethylsulfanyl-6-((R)-1-hydroxy-ethyl)-1-aza-bicyclo[3.2.0]hept-2-en-7-one

(3S,4R)-4-[3-(1-Benzyloxymethyl-1H-tetrazol-5-yl)-3-diazo-2-oxo-propyl]-3-((R)-1-hydroxy-ethyl)-azetidin-2-one