(1R)-2-dimethylcarbamoyl-3-(4-hydroxyphenyl)-cyclopropanecarboxylic acid

Base Information

• Chemical Name: (1R)-2-dimethylcarbamoyl-3-(4-hydroxyphenyl)-cyclopropanecarboxylic acid
• CAS No.: 326473-16-9
• Molecular Formula: C₁₃H₁₅NO₄
• Molecular Weight: 249.266

Synonyms:(1R)-2-dimethylcarbamoyl-3-(4-hydroxyphenyl)-cyclopropanecarboxylic acid

Chemical Property of (1R)-2-dimethylcarbamoyl-3-(4-hydroxyphenyl)-cyclopropanecarboxylic acid

Chemical Property:

Purity/Quality:

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Technology Process of (1R)-2-dimethylcarbamoyl-3-(4-hydroxyphenyl)-cyclopropanecarboxylic acid

There total 10 articles about (1R)-2-dimethylcarbamoyl-3-(4-hydroxyphenyl)-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: 99.0%

(1R)-2-(4-tert-butoxyphenyl)-3-dimethylcarbamoyl-cyclopropanecarboxylic acid → (1R)-2-dimethylcarbamoyl-3-(4-hydroxyphenyl)-cyclopropanecarboxylic acid (326473-16-9)

Guidance literature:

With trifluoroacetic acid; for 0.0833333h;

DOI:10.1021/ja011746f

Reference yield:

4-tert-butoxybromobenzene (60876-70-2) → (1R)-2-dimethylcarbamoyl-3-(4-hydroxyphenyl)-cyclopropanecarboxylic acid (326473-16-9)

Guidance literature:

Multi-step reaction with 9 steps

1.1: magnesium / tetrahydrofuran / 5 h / Heating

1.2: 96 percent / iodine / tetrahydrofuran; diethyl ether / 0.5 h / 0 °C

2.1: 92 percent / copper iodide; pyrrolidine / palladium tetrakistriphenylphosphine / tetrahydrofuran / 36 h

3.1: 93 percent / quinoline; H₂ / Pd/CaCO₃; Pb(OAc)4 / diethyl ether / 0.5 h / 760.05 Torr

4.1: N,N-dimethylaniline / acetonitrile / 0.42 h / -10 °C

4.2: 83 percent / Et₃N; H₂O / acetonitrile

5.1: Rh₂(S-MEPY)4 / CH₂Cl₂ / 37 h

6.1: AlMe₃ / hexane; benzene / 1 h / 10 °C

6.2: 93 percent / benzene / 14 h / 50 °C

7.1: 84 percent / N-methylmorpholine-N-oxide; tetrapropylammonium-perruthenate / CH₂Cl₂ / 1 h / 20 °C

8.1: Et₃N / methanol / 20 h / Heating

8.2: 68 percent / Jones reagent / acetone / 0.75 h / 20 °C

9.1: 99 percent / trifluoroacetic acid / 0.08 h

With pyrrolidine; quinoline; copper(l) iodide; tetrapropylammonium perruthennate; Rh₂[(2S)-5-hydroxypyrrolidine-2-COOMe]4; hydrogen; trimethylaluminum; magnesium; N,N-dimethyl-aniline; 4-methylmorpholine N-oxide; triethylamine; trifluoroacetic acid; lead(IV) acetate; Lindlar's catalyst; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; acetonitrile; benzene;

DOI:10.1021/ja011746f

Reference yield:

1-(tert-butoxy)-4-iodobenzene (329318-60-7) → (1R)-2-dimethylcarbamoyl-3-(4-hydroxyphenyl)-cyclopropanecarboxylic acid (326473-16-9)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 92 percent / copper iodide; pyrrolidine / palladium tetrakistriphenylphosphine / tetrahydrofuran / 36 h

2.1: 93 percent / quinoline; H₂ / Pd/CaCO₃; Pb(OAc)4 / diethyl ether / 0.5 h / 760.05 Torr

3.1: N,N-dimethylaniline / acetonitrile / 0.42 h / -10 °C

3.2: 83 percent / Et₃N; H₂O / acetonitrile

4.1: Rh₂(S-MEPY)4 / CH₂Cl₂ / 37 h

5.1: AlMe₃ / hexane; benzene / 1 h / 10 °C

5.2: 93 percent / benzene / 14 h / 50 °C

6.1: 84 percent / N-methylmorpholine-N-oxide; tetrapropylammonium-perruthenate / CH₂Cl₂ / 1 h / 20 °C

7.1: Et₃N / methanol / 20 h / Heating

7.2: 68 percent / Jones reagent / acetone / 0.75 h / 20 °C

8.1: 99 percent / trifluoroacetic acid / 0.08 h

With pyrrolidine; quinoline; copper(l) iodide; tetrapropylammonium perruthennate; Rh₂[(2S)-5-hydroxypyrrolidine-2-COOMe]4; hydrogen; trimethylaluminum; N,N-dimethyl-aniline; 4-methylmorpholine N-oxide; triethylamine; trifluoroacetic acid; lead(IV) acetate; Lindlar's catalyst; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; acetonitrile; benzene;

DOI:10.1021/ja011746f

upstream raw materials:

4-tert-butoxybromobenzene

1-(tert-butoxy)-4-iodobenzene

3-(4-tert-butoxyphenyl)-2Z-propen-1-ol

3-(4-tert-butoxyphenyl)-prop-2-yne-1-ol

Downstream raw materials:

(1R)-2-dimethylcarbamoyl-3-[4-(dibenzyloxyphosphoryloxy)-phenyl]-cyclopropanecarboxylic acid

(2S,3S)-2-{(S)-4-Benzyloxycarbonyl-2-[(S)-4-benzyloxycarbonyl-2-({(1R,2R,3R)-2-[4-(bis-benzyloxy-phosphoryloxy)-phenyl]-3-dimethylcarbamoyl-cyclopropanecarbonyl}-amino)-butyrylamino]-butyrylamino}-3-methyl-pentanoic acid benzyl ester

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