(1S,2R)-1-Azidocarbonyl-2-(4-hydroxy-phenyl)-cyclopropanecarboxylic acid

Base Information

• Chemical Name: (1S,2R)-1-Azidocarbonyl-2-(4-hydroxy-phenyl)-cyclopropanecarboxylic acid
• CAS No.: 117942-47-9
• Molecular Formula: C₁₁H₉N₃O₄
• Molecular Weight: 247.21
• Mol file: 117942-47-9.mol

Synonyms:(1S,2R)-1-Azidocarbonyl-2-(4-hydroxy-phenyl)-cyclopropanecarboxylic acid

Chemical Property of (1S,2R)-1-Azidocarbonyl-2-(4-hydroxy-phenyl)-cyclopropanecarboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2R)-1-Azidocarbonyl-2-(4-hydroxy-phenyl)-cyclopropanecarboxylic acid

There total 6 articles about (1S,2R)-1-Azidocarbonyl-2-(4-hydroxy-phenyl)-cyclopropanecarboxylic acid 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: 80.0%

Potassium; (1S,2R)-1-hydrazinocarbonyl-2-[4-(2-methoxy-ethoxymethoxy)-phenyl]-cyclopropanecarboxylate (117942-46-8) → (1S,2R)-1-Azidocarbonyl-2-(4-hydroxy-phenyl)-cyclopropanecarboxylic acid (117942-47-9)

Guidance literature:

With sulfuric acid; sodium nitrite; In diethyl ether; water; at 5 ℃; for 24h;

DOI:10.1021/jo00262a033

Reference yield:

diethyl 4-<(2-methoxyethoxy)methoxy>benzalmalonate (117942-42-4) → (1S,2R)-1-Azidocarbonyl-2-(4-hydroxy-phenyl)-cyclopropanecarboxylic acid (117942-47-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 76 percent / dimethylsulfoxide; tetrahydrofuran / 1.) RT, 1 h, 2.) 50 deg C, 1 h

2: 78 percent / NaOH, H₂O / ethanol / 48 h / Ambient temperature

3: 1.) 5percent KHCO₃, 2.) NH₂NH₂*H₂O / 1.) EtOH, water, 2.) reflux, 24 h

4: 80 percent / NaNO₂, H₂SO₄ / diethyl ether; H₂O / 24 h / 5 °C

With sodium hydroxide; sulfuric acid; water; potassium hydrogencarbonate; hydrazine hydrate; sodium nitrite; In tetrahydrofuran; diethyl ether; ethanol; water; dimethyl sulfoxide;

DOI:10.1021/jo00262a033

Reference yield:

(Z)-1-(ethoxycarbonyl)-2-<4-<(2-methoxyethoxy)methoxy>phenyl>cyclopropanecarboxylic acid (117942-44-6) → (1S,2R)-1-Azidocarbonyl-2-(4-hydroxy-phenyl)-cyclopropanecarboxylic acid (117942-47-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) 5percent KHCO₃, 2.) NH₂NH₂*H₂O / 1.) EtOH, water, 2.) reflux, 24 h

2: 80 percent / NaNO₂, H₂SO₄ / diethyl ether; H₂O / 24 h / 5 °C

With sulfuric acid; potassium hydrogencarbonate; hydrazine hydrate; sodium nitrite; In diethyl ether; water;

DOI:10.1021/jo00262a033

upstream raw materials:

Potassium; (1S,2R)-1-hydrazinocarbonyl-2-[4-(2-methoxy-ethoxymethoxy)-phenyl]-cyclopropanecarboxylate

diethyl 4-<(2-methoxyethoxy)methoxy>benzalmalonate

(Z)-1-(ethoxycarbonyl)-2-<4-<(2-methoxyethoxy)methoxy>phenyl>cyclopropanecarboxylic acid

diethyl 2-<4-<(2-methoxyethoxy)methoxy>phenyl>cyclopropane-1,1-dicarboxylate

Downstream raw materials:

(1S,2R)-1-Azidocarbonyl-2-(4-hydroxy-phenyl)-cyclopropanecarboxylic acid methyl ester

N-<<2-(trimethylsilyl)ethoxy>carbonyl>-O-<(2-methoxyethoxy)methyl>-(Z)-2,3-methanotyrosine methyl ester

N-<<2-(Trimethylsilyl)ethoxy>carbonyl>-O-<(2-methoxyethoxy)methyl>-(Z)-2,3-methanotyrosine

(1S,2S)-1-Amino-2-(4-hydroxy-phenyl)-cyclopropanecarboxylic acid; hydrochloride