Unii-9zsq1C4209

Base Information

• Chemical Name: Unii-9zsq1C4209
• CAS No.: 201851-20-9
• Molecular Formula: C₂₀H₁₉NO₅
• Molecular Weight: 353.375
• UNII: 9ZSQ1C4209
• DSSTox Substance ID: DTXSID601336165
• Wikipedia: LY-344545
• Wikidata: Q6460427
• Mol file: 201851-20-9.mol

Synonyms:LY 344545;LY-344545;LY344545

Chemical Property of Unii-9zsq1C4209

Chemical Property:

• XLogP3: -0.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 353.12632271
• Heavy Atom Count: 26
• Complexity: 559

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1C(C1C(CC2C3=CC=CC=C3OC4=CC=CC=C24)(C(=O)O)N)C(=O)O
• Isomeric SMILES: C1[C@H]([C@@H]1[C@@](CC2C3=CC=CC=C3OC4=CC=CC=C24)(C(=O)O)N)C(=O)O

Technology Process of Unii-9zsq1C4209

There total 7 articles about Unii-9zsq1C4209 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: 52.0%

(1S,2S)-2-[(S)-1-(4-Methoxy-benzyl)-2,5-dioxo-4-(9H-xanthen-9-ylmethyl)-imidazolidin-4-yl]-cyclopropanecarboxylic acid 4-methoxy-benzyl ester → 2-[(1S,2S)-2-carboxycyclopropyl]-3-(9H-xanthen-9-yl)-D-alanine (201851-20-9,201943-63-7)

Guidance literature:

With sodium hydroxide; at 200 ℃; for 24h;

DOI:10.1021/jm970498o

Reference yield:

(1R,2R)-cyclopropane-1,2-dicarboxylic acid bis-(1S,2R,5S)-(5-isopropyl-2-methyl-cyclohexyl) ester (96149-01-8) → LY 344545 (201943-63-7,201851-20-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 5 N aq. NaOH / propan-2-ol / 70 °C

2: SOCl₂ / Ambient temperature

3: 1.) Zn(Cu), 2.) Pd(Ph₃P)4 / 1.) benzene, N,N-dimethylacetamide, 60 deg C, 3 h, 2.) benzene, N,N-dimethylacetamide, RT, 1 h

4: 95 percent / 1 N aq. NaOH / ethanol / 23 h / 60 - 65 °C

5: ethanol; H₂O / 120 h / 55 °C

6: 43 percent / KHCO₃ / dimethylformamide / 125 °C

7: 2 percent / aq. Ba(OH)2 / 24 h / 200 °C

With barium dihydroxide; sodium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; thionyl chloride; zinc copper; potassium hydrogencarbonate; In ethanol; water; N,N-dimethyl-formamide; isopropyl alcohol;

DOI:10.1021/jm970498o

Reference yield:

(1R,2R)-cyclopropane-1,2-dicarboxylic acid mono-(1S,2R,5S)-(5-isopropyl-2-methyl-cyclohexyl) ester (175415-91-5) → LY 344545 (201943-63-7,201851-20-9)

Guidance literature:

Multi-step reaction with 6 steps

1: SOCl₂ / Ambient temperature

2: 1.) Zn(Cu), 2.) Pd(Ph₃P)4 / 1.) benzene, N,N-dimethylacetamide, 60 deg C, 3 h, 2.) benzene, N,N-dimethylacetamide, RT, 1 h

3: 95 percent / 1 N aq. NaOH / ethanol / 23 h / 60 - 65 °C

4: ethanol; H₂O / 120 h / 55 °C

5: 43 percent / KHCO₃ / dimethylformamide / 125 °C

6: 2 percent / aq. Ba(OH)2 / 24 h / 200 °C

With barium dihydroxide; sodium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; thionyl chloride; zinc copper; potassium hydrogencarbonate; In ethanol; water; N,N-dimethyl-formamide;

DOI:10.1021/jm970498o

upstream raw materials:

(1R,2R)-cyclopropane-1,2-dicarboxylic acid bis-(1S,2R,5S)-(5-isopropyl-2-methyl-cyclohexyl) ester

(1R,2R)-cyclopropane-1,2-dicarboxylic acid mono-(1S,2R,5S)-(5-isopropyl-2-methyl-cyclohexyl) ester

(1R,2R)-2-chlorocarbonyl-cyclopropanecarboxylic acid (1S,2R,5S)-5-isopropyl-2-methyl-cyclohexyl ester

(1R,2R)-2-(2-9H-Xanthen-9-yl-acetyl)-cyclopropanecarboxylic acid

Refernces