(1R)-2-(4-tert-butoxyphenyl)-3-hydroxymethylcyclopropanecarboxylic acid-(2,4-dimethoxy-benzyl)-methyl amide

Base Information

• Chemical Name: (1R)-2-(4-tert-butoxyphenyl)-3-hydroxymethylcyclopropanecarboxylic acid-(2,4-dimethoxy-benzyl)-methyl amide
• CAS No.: 397883-55-5
• Molecular Formula: C₂₅H₃₃NO₅
• Molecular Weight: 427.541

Synonyms:(1R)-2-(4-tert-butoxyphenyl)-3-hydroxymethylcyclopropanecarboxylic acid-(2,4-dimethoxy-benzyl)-methyl amide

Chemical Property of (1R)-2-(4-tert-butoxyphenyl)-3-hydroxymethylcyclopropanecarboxylic acid-(2,4-dimethoxy-benzyl)-methyl amide

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (1R)-2-(4-tert-butoxyphenyl)-3-hydroxymethylcyclopropanecarboxylic acid-(2,4-dimethoxy-benzyl)-methyl amide

There total 7 articles about (1R)-2-(4-tert-butoxyphenyl)-3-hydroxymethylcyclopropanecarboxylic acid-(2,4-dimethoxy-benzyl)-methyl amide 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: 67.0%

N-(2,4-dimethoxybenzyl)-N-methylammonium chloride + (1R)-6-(4-tert-butoxyphenyl)-3-oxabicyclo[3.1.0]hexan-2-one (326473-12-5) → (1R)-2-(4-tert-butoxyphenyl)-3-hydroxymethylcyclopropanecarboxylic acid-(2,4-dimethoxy-benzyl)-methyl amide (397883-55-5)

Guidance literature:

N-(2,4-dimethoxybenzyl)-N-methylammonium chloride; With trimethylaluminum; In hexane; benzene; at 10 ℃; for 1h;

(1R)-6-(4-tert-butoxyphenyl)-3-oxabicyclo[3.1.0]hexan-2-one; In benzene; at 50 ℃; for 14h; Further stages.;

DOI:10.1021/ja011746f

Reference yield:

4-tert-butoxybromobenzene (60876-70-2) → (1R)-2-(4-tert-butoxyphenyl)-3-hydroxymethylcyclopropanecarboxylic acid-(2,4-dimethoxy-benzyl)-methyl amide (397883-55-5)

Guidance literature:

Multi-step reaction with 6 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: 67 percent / benzene / 14 h / 50 °C

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

DOI:10.1021/ja011746f

Reference yield:

1-(tert-butoxy)-4-iodobenzene (329318-60-7) → (1R)-2-(4-tert-butoxyphenyl)-3-hydroxymethylcyclopropanecarboxylic acid-(2,4-dimethoxy-benzyl)-methyl amide (397883-55-5)

Guidance literature:

Multi-step reaction with 5 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: 67 percent / benzene / 14 h / 50 °C

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

DOI:10.1021/ja011746f

upstream raw materials:

1-(2,4-dimethoxyphenyl)-N-methylmethanamine

(1R)-6-(4-tert-butoxyphenyl)-3-oxabicyclo[3.1.0]hexan-2-one

4-tert-butoxybromobenzene

1-(tert-butoxy)-4-iodobenzene

Downstream raw materials:

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

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

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

(1R)-2-(4-tert-butoxyphenyl)-3-formyl-cyclopropanecarboxylic acid (2,4-dimethoxybenzyl)-methyl amide

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