1-{[(2S,4R)-1-[(S)-2-((S)-2-Acetylamino-2-cyclohexyl-acetylamino)-3-methyl-butyryl]-4-(naphthalen-1-ylmethoxy)-pyrrolidine-2-carbonyl]-amino}-2-ethyl-cyclopropanecarboxylic acid methyl ester

Base Information

• Chemical Name: 1-{[(2S,4R)-1-[(S)-2-((S)-2-Acetylamino-2-cyclohexyl-acetylamino)-3-methyl-butyryl]-4-(naphthalen-1-ylmethoxy)-pyrrolidine-2-carbonyl]-amino}-2-ethyl-cyclopropanecarboxylic acid methyl ester
• CAS No.: 693785-71-6
• Molecular Formula: C₃₈H₅₂N₄O₇
• Molecular Weight: 676.853

Synonyms:1-{[(2S,4R)-1-[(S)-2-((S)-2-Acetylamino-2-cyclohexyl-acetylamino)-3-methyl-butyryl]-4-(naphthalen-1-ylmethoxy)-pyrrolidine-2-carbonyl]-amino}-2-ethyl-cyclopropanecarboxylic acid methyl ester

Chemical Property of 1-{[(2S,4R)-1-[(S)-2-((S)-2-Acetylamino-2-cyclohexyl-acetylamino)-3-methyl-butyryl]-4-(naphthalen-1-ylmethoxy)-pyrrolidine-2-carbonyl]-amino}-2-ethyl-cyclopropanecarboxylic acid methyl ester

Chemical Property:

Purity/Quality:

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Technology Process of 1-{[(2S,4R)-1-[(S)-2-((S)-2-Acetylamino-2-cyclohexyl-acetylamino)-3-methyl-butyryl]-4-(naphthalen-1-ylmethoxy)-pyrrolidine-2-carbonyl]-amino}-2-ethyl-cyclopropanecarboxylic acid methyl ester

There total 12 articles about 1-{[(2S,4R)-1-[(S)-2-((S)-2-Acetylamino-2-cyclohexyl-acetylamino)-3-methyl-butyryl]-4-(naphthalen-1-ylmethoxy)-pyrrolidine-2-carbonyl]-amino}-2-ethyl-cyclopropanecarboxylic acid methyl ester 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:

methyl (1RS,2RS)-1-Boc-amino-2-ethylcyclopropanecarboxylate + Ac-Chg-Val-Pro-(4R)-(1-naphthylmethoxy)-OH (693785-68-1) → 1-{[(2S,4R)-1-[(S)-2-((S)-2-Acetylamino-2-cyclohexyl-acetylamino)-3-methyl-butyryl]-4-(naphthalen-1-ylmethoxy)-pyrrolidine-2-carbonyl]-amino}-2-ethyl-cyclopropanecarboxylic acid methyl ester (693785-71-6)

Guidance literature:

methyl (1RS,2RS)-1-Boc-amino-2-ethylcyclopropanecarboxylate; With hydrogenchloride; In 1,4-dioxane; at 20 ℃; for 0.5h;

Ac-Chg-Val-Pro-(4R)-(1-naphthylmethoxy)-OH; With 4-methyl-morpholine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In dichloromethane; at 20 ℃;

DOI:10.1021/jm030573x

Reference yield:

t-Boc-L-valine (13734-41-3) → 1-{[(2S,4R)-1-[(S)-2-((S)-2-Acetylamino-2-cyclohexyl-acetylamino)-3-methyl-butyryl]-4-(naphthalen-1-ylmethoxy)-pyrrolidine-2-carbonyl]-amino}-2-ethyl-cyclopropanecarboxylic acid methyl ester (693785-71-6)

Guidance literature:

Multi-step reaction with 7 steps

1.1: NMM; TBTU / CH₂Cl₂ / 3.5 h

2.1: aq. HCl / dioxane / 0.5 h / 20 °C

3.1: NMM; TBTU / CH₂Cl₂; H₂O / 3.5 h

4.1: aq. HCl / dioxane / 0.5 h / 20 °C

5.1: 3.39 g / NMM / CH₂Cl₂

6.1: 95 percent / Pd(PPh₃)4; PPh₃; pyrrolidine / acetonitrile; CH₂Cl₂ / 20 °C

7.1: aq. HCl / dioxane / 0.5 h / 20 °C

7.2: NMM; HATU / CH₂Cl₂ / 20 °C

With pyrrolidine; 4-methyl-morpholine; hydrogenchloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triphenylphosphine; In 1,4-dioxane; dichloromethane; water; acetonitrile;

DOI:10.1021/jm030573x

Reference yield:

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid (13726-69-7,946610-68-0) → 1-{[(2S,4R)-1-[(S)-2-((S)-2-Acetylamino-2-cyclohexyl-acetylamino)-3-methyl-butyryl]-4-(naphthalen-1-ylmethoxy)-pyrrolidine-2-carbonyl]-amino}-2-ethyl-cyclopropanecarboxylic acid methyl ester (693785-71-6)

Guidance literature:

Multi-step reaction with 10 steps

1.1: NaH / tetrahydrofuran / 1 h / 20 °C

1.2: 58 percent / tetrahydrofuran / 18 h / Heating

2.1: 85 percent / DBU / acetonitrile / 24 h / 20 °C

3.1: aq. HCl / dioxane / 0.5 h / 20 °C

4.1: NMM; TBTU / CH₂Cl₂ / 3.5 h

5.1: aq. HCl / dioxane / 0.5 h / 20 °C

6.1: NMM; TBTU / CH₂Cl₂; H₂O / 3.5 h

7.1: aq. HCl / dioxane / 0.5 h / 20 °C

8.1: 3.39 g / NMM / CH₂Cl₂

9.1: 95 percent / Pd(PPh₃)4; PPh₃; pyrrolidine / acetonitrile; CH₂Cl₂ / 20 °C

10.1: aq. HCl / dioxane / 0.5 h / 20 °C

10.2: NMM; HATU / CH₂Cl₂ / 20 °C

With pyrrolidine; 4-methyl-morpholine; hydrogenchloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium hydride; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; acetonitrile;

DOI:10.1021/jm030573x

upstream raw materials:

Ac-Chg-Val-Pro-(4R)-(1-naphthylmethoxy)-OH

t-Boc-L-valine

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

2-(bromomethyl)naphthalene

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